original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
253,052 | ord_dataset-49bd993346b64eeeb2a8fe2643164a0a | null | 1992-01-01T00:08:00 | true | [N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([NH:17][C:18](=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:21][CH:20]=2)[CH:5]=1)([O-])=O>C(O)C.O1CCCC1.[C].[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7](... | CCOC(=O)COc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc(OCCCCc2ccccc2)cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | To a mixture of 2.81 g of ethyl 4-nitro-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate obtained in Example 26 in 50 ml of ethanol-tetrahydrofuran (1:1) was added 0.5 g of 10% palladium-carbon. Catalytic reduction was performed at room temperature under normal pressure until absorption of hydrogen was discontinued. The c... | CCOC(=O)COc1ccc(N)cc1NC(=O)c1ccc(OCCCCc2ccccc2)cc1 | null | 65.2 | null |
1,675,392 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH3:1][NH2:2].[CH:3]1([C@H:6]([NH:8][C:9]2[C:10]3[N:11]([CH:18]=[C:19]([C:21]4[O:22][C:23](SC)=[N:24][N:25]=4)[CH:20]=3)[N:12]=[CH:13][C:14]=2[C:15]([NH2:17])=[O:16])[CH3:7])[CH2:5][CH2:4]1>>[CH:3]1([C@H:6]([NH:8][C:9]2[C:10]3[N:11]([CH:18]=[C:19]([C:21]4[O:22][C:23]([NH:2][CH3:1])=[N:24][N:25]=4)[CH:20]=3)[N:12]=[CH:... | CN | CSc1nnc(-c2cc3c(N[C@H](C)C4CC4)c(C(N)=O)cnn3c2)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 200 | 0.42 | Methylamine (2 mL, 16 mmol, 8.0M solution in ethanol) was added in one portion to (R)-4-(1-cyclopropylethylamino)-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (7 mg, 0.018 mmol). The resulting mixture was heated in the CEM microwave at 200° C. for 1 hour. The crude material was purified... | CNc1nnc(-c2cc3c(N[C@H](C)C4CC4)c(C(N)=O)cnn3c2)o1 | null | 50.5 | null |
1,754,311 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([O:13]C)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1 | COC(=O)/C=C/c1cc(Cl)cc(Cl)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To (E)-methyl 3-(3,5-dichlorophenyl)acrylate (step 1) (2 g, 8.66 mmol) in THF (35 ml) was added 2M NaOH (12.98 ml, 26.0 mmol) and the reaction mixture was stirred at RT overnight. The solvent was removed under reduced pressure and the residue was dissolved in water and washed with EtOAc. The aqueous portion was acidifi... | O=C(O)/C=C/c1cc(Cl)cc(Cl)c1 | null | null | null |
1,012,029 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH2:1]([O:4][C:5](=[O:17])[C:6]([C:15]#[N:16])=[C:7](O)[CH:8]([CH2:11][S:12][CH3:13])[CH2:9][CH3:10])[CH2:2][CH3:3].O=P(Cl)(Cl)Cl.C([N:25](CC)CC)C>C(Cl)Cl>[NH2:25]/[C:7](/[CH:8]([CH2:11][S:12][CH3:13])[CH2:9][CH3:10])=[C:6](/[C:15]#[N:16])\[C:5]([O:4][CH2:1][CH2:2][CH3:3])=[O:17] | CCCOC(=O)C(C#N)=C(O)C(CC)CSC | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | 15 g (58.3 mmol) of n-propyl-2-cyano-3-hydroxy-4-[(methyl-sulfanyl)methyl]-2-hexenoate were dissolved in CH2Cl2, and 18 g (0.12 mmol) of POCl3 were added. At 0° C., 24 g (237 mmol) of triethylamine were then added dropwise, and the mixture was stirred at 25° C. for 2 h. The reaction solution was concentrated and the re... | CCCOC(=O)/C(C#N)=C(\N)C(CC)CSC | null | null | null |
684,590 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH3:16].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:14][CH2:15][CH3:16])=[CH:12][CH:11]=1)[CH3:10] | CCOC(=O)c1ccc(O)cc1 | CCCBr | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | (Scheme 1, Compound A) To a solution of ethyl 4-hydroxybenzoate (2.0 g, 12 mmol) and bromopropane (4.0 g, 32.8 mmol) in DMF (50 mL) was added NaH (60% in mineral oil, 0.80 g, 20.8 mmol). The resultant suspension was stirred at room temperature for 1.0 hour. The mixture was diluted with ethyl acetate (EtOAc) (300 mL), w... | CCCOc1ccc(C(=O)OCC)cc1 | null | 90.8 | null |
1,293,784 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[C:8]([Cl:19])[N:9]=[C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[NH2:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23]>>[Cl:19][C:8]1[N:9]=[C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:11]2[N:12]=[C:3]([CH2:2][NH:20][CH2:21][C:22]([CH3:25])([OH:24... | CC(C)(O)CN | Clc1nc(N2CCOCC2)c2nc(CBr)ccc2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-(6-(Bromomethyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine 7 (0.3 g) was reacted with 1-amino-2-methylpropan-2-ol via General Procedure B to afford quantitative yield of 1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylamino)-2-methylpropan-2-ol. | CC(C)(O)CNCc1ccc2nc(Cl)nc(N3CCOCC3)c2n1 | null | null | null |
1,585,950 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH2:1]([O:3][C:4](=[O:62])[CH2:5][N:6]([C:8](=[O:61])[C@@H:9]([NH:25][C:26](=[O:60])[C@@H:27]([NH:52]C(OC(C)(C)C)=O)[CH2:28][CH2:29][CH2:30][NH:31]/[C:32](/[NH2:51])=[N:33]\[S:34]([C:37]1[C:38]([CH3:50])=[C:39]([CH3:49])[C:40]2[O:44][C:43]([CH3:46])([CH3:45])[CH2:42][C:41]=2[C:47]=1[CH3:48])(=[O:36])=[O:35])[CH2:10][N... | CCOC(=O)CN(C)C(=O)[C@H](CN(C)S(=O)(=O)c1ccccc1[N+](=O)[O-])NC(=O)[C@H](CCCN/C(N)=N\S(=O)(=O)c1c(C)c(C)c2c(c1C)CC(C)(C)O2)NC(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 1 | Compound E (7.4 g, 8.2 mmol) in DCM (24 mL) was treated with 4 M HCl in dioxane (24 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 h. DCM and most of the dioxane were removed in vacuo to a total volume of ˜15 mL, and Et2O (300 mL) was added. Precipitated product was filtered o... | CCOC(=O)CN(C)C(=O)[C@H](CN(C)S(=O)(=O)c1ccccc1[N+](=O)[O-])NC(=O)[C@@H](N)CCCN/C(N)=N\S(=O)(=O)c1c(C)c(C)c2c(c1C)CC(C)(C)O2 | null | 95.3 | null |
1,562,723 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | CCN(C(C)C)C(C)C.[C:10]([C:13]1[CH:18]=[N:17][N:16]2[CH:19]=[C:20]([C:22]3[CH:23]=[N:24][N:25]([CH2:27][C:28](O)=[O:29])[CH:26]=3)[CH:21]=[C:15]2[C:14]=1[NH:31][C@H:32]1[C@@H:36]([CH3:37])[CH2:35][N:34]([C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][N:39]=2)[CH2:33]1)(=[O:12])[NH2:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](... | FC1(F)CNC1 | C[C@H]1CN(c2ccc(C#N)cn2)C[C@H]1Nc1c(C(N)=O)cnn2cc(-c3cnn(CC(=O)O)c3)cc12 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | 2.5 | Hunig's base (0.014 mL, 0.079 mmol) was added to a stirred solution of crude 2-(4-(3-carbamoyl-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazin-6-yl)-1H-pyrazol-1-yl)acetic acid (20 mg, from Step 2) and HATU (20.05 mg, 0.053 mmol). After 2.5 h at room temperature, 3,3-difluoroaz... | C[C@H]1CN(c2ccc(C#N)cn2)C[C@H]1Nc1c(C(N)=O)cnn2cc(-c3cnn(CC(=O)N4CC(F)(F)C4)c3)cc12 | null | 17.8 | null |
1,042,223 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | C[O:2][C:3]1[N:8]=[C:7]([O:9]C)[C:6]([C:11]2[O:15][C:14]([C:16](=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:13][CH:12]=2)=[CH:5][N:4]=1>CCOC(C)=O>[C:23]1([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]([C:14]2[O:15][C:11]([C:6]3[C:7](=[O:9])[NH:8][C:... | COc1ncc(-c2cnc(C(=O)CCCCCCc3ccccc3)o2)c(OC)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 1-(5-(2,4-dimethoxypyrimidin-5-yl)oxazol-2-yl)-7-phenylheptan-1-one (15 mg, 0.038 mmol) following General Procedure H. Flash chromatography (EtOAc) yielded the title compound as a white solid (10 mg, 71%): 1H NMR (CDCl3, 400 MHz) δ 7.90 (s, 1H), 7.71 (s, 1H), 7.28-7.24 (m, 2H), 7.18... | O=C(CCCCCCc1ccccc1)c1ncc(-c2c[nH]c(=O)[nH]c2=O)o1 | null | 71.6 | null |
930,672 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [CH3:1][O:2][C:3]([C:5]1[S:6][C:7](N)=[C:8]([C:20]#[N:21])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][CH:11]=1)=[O:4].[I:23]CI.N(OCCC(C)C)=O>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([I:23])=[C:8]([C:20]#[N:21])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[... | ICI | COC(=O)c1sc(N)c(C#N)c1-c1ccc(C(C)(C)C)cc1 | null | CC(C)CCON=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 100 | 0.25 | Combine 5-amino-3-(4-tert-butyl-phenyl)-4-cyano-thiophene-2-carboxylic acid methyl ester (0.29 mmol) in acetonitrile and add diiodomethane (1.02 mmol) and iso-amyl nitrite (0.73 mmol) and heat to 100° C. After 15 minutes, cool the reaction slowly to room temperature and stir an additional 1 hour. Concentrate the reacti... | COC(=O)c1sc(I)c(C#N)c1-c1ccc(C(C)(C)C)cc1 | null | null | null |
971,669 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])\[CH3:7])[CH3:2].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])\[CH2:7][Br:18]... | CCOC(=O)/C=C(\C)Oc1ccc(Cl)cc1Cl | O=C1CCC(=O)N1Br | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred mixture of (E)-3-(2,4-dichloro-phenoxy)-but-2-enoic acid ethyl ester (4.00 g, 0.015 mol) in carbon tetrachloride (25 mL) under a nitrogen atmosphere was added N-bromosuccinimide (2.32 g, 0.013 mol) and benzoyl peroxide (280 mg, 0.001 mol). Nitrogen gas was bubbled through the mixture for 5 min, and the res... | CCOC(=O)/C=C(\CBr)Oc1ccc(Cl)cc1Cl | null | 65.2 | null |
1,313,420 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[I-].[CH2:49]([N+:53]1[N:57]=[C:56]([CH3:58])[S:55][C:54]=1[CH3:59])[CH2:50][CH2:51][CH3:52]>>[CH2:49]([N:53]1[N:57]=[C:56]([CH3:58])[S:55]/[C:54]/1=[CH:59]\[C... | CCCC[n+]1nc(C)sc1C | O=C(O)c1cc(C(F)(F)F)ccc1F | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 25 | 8 | In a 20 mL vial 2-fluoro-5-(trifluoromethyl)benzoic acid (0.9 mL of 0.2 M in DMA, 1.10 equiv) was added followed by the addition of HATU (76 mg in 0.7 mL of DMA, 0.2 mmol, 1.20 equiv.), DIEA (51 mg in 0.7 mL of DMA, 0.4 mmol, 2.40 equiv.), and finally 3-butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide (49 mg in 0.7 mL ... | CCCCN1N=C(C)S/C1=C\C(=O)c1cc(C(F)(F)F)ccc1F | null | null | null |
1,252,168 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [NH2:1][C@H:2]1[C:10]2[C:5](=[C:6]([C:11]3[N:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH:23]=4)[C:21]#[N:22])[O:13][N:12]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:37][S:38]([CH:41]=[CH2:42])(=[O:40])=[O:39]>CC(N(C)C)=O>[CH:25]([O:24][C:19]1[CH:18]=[CH:17][C:16... | CC(C)Oc1ccc(-c2nc(-c3cccc4c3CC[C@H]4N)no2)cc1C#N | C=CS(C)(=O)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 80 | null | To a solution of (R)-5-(3-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile 49 (18 mg, 0.05 mmol) in DMA (0.5 mL) was added DIEA (87 μL, 0.5 mmol) and methylvinylsulfone (53 mg, 0.5 mmol). The reaction was heated to 80° C. for 24 h. The crude reaction mixture was purified by preparative... | CC(C)Oc1ccc(-c2nc(-c3cccc4c3CC[C@H]4NCCS(C)(=O)=O)no2)cc1C#N | null | null | null |
59,347 | ord_dataset-28b19b59e93c47698a5a2b21048ec201 | null | 1979-01-01T00:10:00 | true | [Mg].C(I)C.C([C:7]1([OH:21])[CH2:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[S:10][C:9]2[S:18][CH:19]=[CH:20][C:8]1=2)C>CCOCC>[S:18]1[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[CH2:13][C:7](=[O:21])[C:8]=2[CH:20]=[CH:19]1 | CCC1(O)Cc2ccccc2Sc2sccc21 | null | null | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CCI | null | null | null | null | null | null | null | null | null | null | null | From 4.9 g (0.2 mole) of magnesium, 31.2 g (0.2 mole) of ethyl iodide in abs. ether and 23.2 g (0.1 mole) of benzo[f]thieno[2,3-b]thiepin-4(5H)-one, there is obtained 4-ethyl-4,5-dihydro-benzo[f]thieno[2,3-b]thiepin-4-ol as an oily crude product. | O=C1Cc2ccccc2Sc2sccc21 | null | null | null |
394,499 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [CH2:1]([N:3]1[C:11]2[C:10](=[O:12])[NH:9][C:8](=[O:13])[N:7]([CH3:14])[C:6]=2[N:5]=[CH:4]1)[CH3:2].Br[CH2:16][CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])(=[O:23])[O:20][CH2:21][CH3:22]>>[CH2:1]([N:3]1[C:11]2[C:10](=[O:12])[N:9]([CH2:16][CH2:17][CH2:18][P:19](=[O:23])([O:24][CH2:25][CH3:26])[O:20][CH2:21][CH3:22])[C:... | CCOP(=O)(CCCBr)OCC | CCn1cnc2c1c(=O)[nH]c(=O)n2C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title substance was prepared from 0.041 mol of 7-ethyl-3-methyl-xanthine and 0.049 mol of diethyl 3-bromopropanephosphonate analogously to Example 32. | CCOP(=O)(CCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC | null | null | null |
1,038,237 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH:1]([N:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[N:15]=[N:16][N:17]([C:20]4[C:21]([F:26])=[N:22][CH:23]=[CH:24][CH:25]=4)[C:18]=3[CH3:19])[CH:10]=2)[C:5]1=[O:27])([CH3:3])[CH3:2].[H][H]>[C].[Pd].C(O)C>[CH:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[N:15]=[N:16][N:17]([C:20]4[C:... | [H][H] | Cc1c(-c2ccc3c(=O)n(C(C)C)ccc3c2)nnn1-c1cccnc1F | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 30 mg of palladium carbon was added to 10 ml of ethanol solution with 10 mg of 4-(2-isopropyl-1-oxo-isoquinoline-6-yl)-1-(2-fluoropyridine-3-yl)-5-methyl-1H-[1,2,3]triazole, and hydrogen was added under 4 atm of hydrogen pressure. 8 hours later, the reaction solution was filtrated and after distilling out the solvents ... | Cc1c(-c2ccc3c(c2)CCN(C(C)C)C3=O)nnn1-c1cccnc1F | null | 69.6 | null |
178,069 | ord_dataset-3ef78abb9a384506b240a419b70e6ceb | null | 1988-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH:18]([C:24]([CH3:26])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:18]([C:24](=[O:25])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:7])=[CH:4][CH:3]=1 | CCOC(=O)C(Cl)C(C)=O | O=C(O)c1ccc(Cl)cc1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | null | A solution of 15.65 g (0.1 mol) of 4-chlorobenzoic acid in 20 ml of dimethylformamide was added dropwise to a stirred suspension of 5.3 g (0.05 mol) of anhydrous sodium carbonate in 80 ml of dimethylformamide. The suspension was heated at 80° C. for 1 hour and a solution of 16.46 g (0.1 mol) of ethyl 2-chloroacetoaceta... | CCOC(=O)C(OC(=O)c1ccc(Cl)cc1)C(C)=O | null | 94.3 | null |
523,487 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10](CO)=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].[C:28]([Br:32])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26... | COC(=O)[C@H](CCSC)NC(=O)c1ccc(CO)cc1-c1ccccc1C | BrC(Br)(Br)Br | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | -10 | 1 | To a stirred solution at −10° C. under N2 of N-[4-hydroxymethyl-2-(2-methylphenyl)benzoyl]methionine methyl ester (200 mg, 0.517 mmol ), prepared as in Example 403F, and carbon tetrabromide (189 mg, 0.568 mmol) in CH2Cl2 (5 mL) was added triphenylphosphine (163 mg, 0.620 mmol). Reaction stirred one hour at −10° C., and... | COC(=O)[C@H](CCSC)NC(=O)c1cccc(CBr)c1-c1ccccc1C | null | null | null |
534,466 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O-])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH:5]=[CH:6][CH:7]=1.Cl.CN(C)CCCN=C=NCC.[C:38]1([CH:44]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:45][CH2:46][NH2:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:... | NCCC(c1ccccc1)c1ccccc1 | CC1=C(C(=O)[O-])C(c2cccc(Cl)c2)C(C(=O)OCCC#N)=C(C)N1 | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 219 mg (0.61 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 138 mg (0.72 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 201 mg (0.95 mmol) of 3,3-diphenylpropylamine and 20 mg (0.16 mmol) of 4-dimethylaminopyridine were stirred in 10 ml of dichl... | CC1=C(C(=O)NCCC(c2ccccc2)c2ccccc2)C(c2cccc(Cl)c2)C(C(=O)OCCC#N)=C(C)N1 | null | null | null |
1,447,556 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28]>>[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([C:6]2[CH:7... | CS(=O)(=O)c1ccc(B(O)O)cc1 | Cc1ccccc1C(CC(=NO)c1ccncc1)c1cccc(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to example 22, from 3-(3-bromo-phenyl)-1-pyridin-4-yl-3-o-tolyl-propan-1-one oxime (example 11) and (4-methylsulfonylphenyl)boronic acid was prepared the title compound as a mixture of E and Z isomers (3:1) as a yellow oil, MS (ESI+): m/z=471.1 ([M+H]+). | Cc1ccccc1C(CC(=NO)c1ccncc1)c1cccc(-c2ccc(S(C)(=O)=O)cc2)c1 | null | null | null |
28,183 | ord_dataset-2cb52357eb5f43c2be56ad5c0662f18f | null | 1977-01-01T00:08:00 | true | [C:1]([C:5]1[S:9][C:8]([N:10]2[CH:15]([OH:16])[CH2:14][CH2:13][N:12]([CH3:17])[C:11]2=[O:18])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>N1C=CC=CC=1>[C:1]([C:5]1[S:9][C:8]([N:10]2[CH:15]([O:16][C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C... | CN1CCC(O)N(c2nnc(C(C)(C)C)s2)C1=O | O=C(Cl)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | Tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone (0.05 mole) dissolved in pyridine (80 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The solution is cooled to a temperature of about 10° C. and benzyl chloroformate (0.06 mole) dissolve... | CN1CCC(OC(=O)OCc2ccccc2)N(c2nnc(C(C)(C)C)s2)C1=O | null | null | null |
1,747,251 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [N:1]([CH:4]1[CH2:8][O:7][CH:6]2[CH:9]([O:12][CH2:13][CH2:14][O:15]CC3C=CC=CC=3)[CH2:10][O:11][CH:5]12)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH:4]1[CH:5]2[O:11][CH2:10][CH:9]([O:12][CH2:13][CH2:14][OH:15])[CH:6]2[O:7][CH2:8]1 | [N-]=[N+]=NC1COC2C(OCCOCc3ccccc3)COC12 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a suspension of 3-azido-6-(2-(benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan (crude product) in MeOH (20 mL) was added Pd/C (10%, 0.31 g). The mixture was stirred at room temperature under a H2 atmosphere overnight. The mixture was filtered and washed with MeOH (20 mL). The filtrate was concentrated in vacuo to give the... | NC1COC2C(OCCO)COC12 | null | null | null |
1,768,521 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[CH:26]([N:29]1[CH:33]=[N:32][N:31]=[C:30]1[C:34]1[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=1[NH2:36])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs... | FC(F)(F)Oc1ccc(-n2cnc(-c3ccc(N=C=S)cc3)n2)cc1 | CC(C)n1cnnc1-c1ccccc1N | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | 3-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (WO 2011/017513) (0.088 g, 0.24 mmol), 2-(4-isopropyl-4H-1,2,4-triazol-3-yl)aniline (0.080 g, 0.40 mmol), and cesium carbonate (0.16 g, 0.50 mmol) in isopropyl alcohol (1.2 mL) was stirred at room temperature overnight. The reaction was diluted... | CC(C)n1cnnc1-c1ccccc1NC(=S)Nc1ccc(-c2ncn(-c3ccc(OC(F)(F)F)cc3)n2)cc1 | null | 20.7 | null |
307,629 | ord_dataset-acbdbaa766314b66a982823354e82bf2 | null | 1995-01-01T00:04:00 | true | [F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19](=[O:20])[CH:18]=[C:17]([CH3:21])[NH:16][C:15]=3[CH3:22])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:27][C:18]1[C:19](=[O:20])[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:2... | O=C1CCC(=O)N1Br | Cc1cc(=O)c(-c2ccc(Oc3ccc(C(F)(F)F)cc3)cc2)c(C)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred suspension of 3-(4-(4-trifluoromethylphenoxy)phenyl)-2,6-dimethyl pyridin-4(1H)-one (4.12 g) in chloroform (50 ml) at room temperature was added N-bromosuccinimide (2.25 g). After 2 hr the mixture was filtered and the solid washed with chlorofrom and dried in vacuo. Recrystallisation from DMF afforded the ... | Cc1[nH]c(C)c(-c2ccc(Oc3ccc(C(F)(F)F)cc3)cc2)c(=O)c1Br | null | 43.4 | null |
1,509,176 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | COC1C=C(OC)C=CC=1C[N:6]([C:30]1[CH:35]=[CH:34][N:33]=[CH:32][N:31]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13]([O:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)=[CH:12][C:11]=1[F:29])(=[O:9])=[O:8].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[F:29][C:11]1[CH:12]=[C:13]([O:17][C@H:... | COc1ccc(CN(c2ccncn2)S(=O)(=O)c2cc(F)c(O[C@H]3CCCC[C@@H]3n3ccnc3)cc2F)c(OC)c1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | The reaction and aftertreatment were conducted in the same manner as in Example 1b by using the N-(2,4-dimethoxybenzyl)-2,5-difluoro-4-{[(1S*,2S*)-2-(1H-imidazol-1-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide (315 mg, 0.538 mmol) prepared in Example 32a, triethylsilane (0.40 mL), trifluoroacetic acid (4.0 mL... | O=S(=O)(Nc1ccncn1)c1cc(F)c(O[C@H]2CCCC[C@H]2n2ccnc2)cc1F | null | 93.9 | null |
613,282 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [NH2:1][CH2:2][CH2:3][C:4]1[N:5]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)=[CH:10][C:9]([Cl:26])=[CH:8][CH:7]=2.[Cl:40][C:41]1[CH:42]=[C:43]([S:48... | O=S(=O)(Cl)c1cc(Cl)cc(Cl)c1 | COC(=O)c1ccc(OCCc2c(CCN)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | To the methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate (Step 5, Example 1)was added 3,5-dichlorobenzenesulfonyl chloride according to the procedure in Example 1 Step 7 to generate the product in 60% yield. | O=C(O)c1ccc(OCCc2c(CCNS(=O)(=O)c3cc(Cl)cc(Cl)c3)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1 | null | 60 | null |
242,847 | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | null | 1992-01-01T00:03:00 | true | [H-].[Na+].[F:3][C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[O:9][C:10](=O)[NH:11][C:6]=2[CH:5]=1.[CH2:16](Br)[CH:17]=C.O>CN(C)C=O>[CH2:10]([NH:11][C:6]1[C:7](=[CH:14][CH:15]=[C:4]([F:3])[CH:5]=1)[C:8]([OH:9])=[O:13])[CH:16]=[CH2:17] | C=CCBr | O=c1[nH]c2cc(F)ccc2c(=O)o1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 1 | Sodium hydride (0.41 g of 80% suspension in oil) was added to a solution of 7-fluoro-1H-3,1-benzoxazine-2,4-dione (2.5 g) in dimethylformamide (30 ml). The mixture was cooled to keep the temperature below 30° and then stirred for 1 hour until a clear solution was obtained. A solution of allyl bromide (1.2 ml) in dimeth... | C=CCNc1cc(F)ccc1C(=O)O | null | null | null |
446,345 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [Cl:1][C:2]1[C:7]([N+:8]([O-])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[H][H]>[Pt].CN1CCOCC1>[OH:9][NH:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1 | O=[N+]([O-])c1cccnc1Cl | [H][H] | null | [Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | 1.5 | A mixture of 18.3 g (115 mmol) of 2-chloro-3-nitropyridine and 300 ml of N-methylmorpholine was hydrogenated at room temperature and a hydrogen pressure of approximately 1.1 bar in the presence of 3 g of 5% platinum/charcoal (55.5% of water [Degussa]). After approximately 1.5 hours, the hydrogen uptake had ceased. The ... | ONc1cccnc1Cl | null | 95.6 | null |
1,547,061 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Br[C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[S:7][C:8]([C:14]4[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=[CH:16][N:15]=4)=[CH:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26]>>[CH:19]([N:18]1[C:14]([C:8]2[S:7][C:6]3[C:5]4[CH:22]=[CH:23][C:2]([C:32]... | CC(C)n1ncnc1-c1cc2c(s1)-c1ccc(Br)cc1OCC2 | CS(=O)(=O)c1cccc(B(O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure for 114, 5 5-(8-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulen-2-yl)-1-isopropyl-1H-[1,2,4]triazole was reacted with 3-methylsulfonylphenylboronic acid to give 146. MS(ESI+) 466.1. | CC(C)n1ncnc1-c1cc2c(s1)-c1ccc(-c3cccc(S(C)(=O)=O)c3)cc1OCC2 | null | null | null |
1,083,898 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | N=C=N.[CH3:4][N:5]([C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1)[CH2:6][CH2:7][NH2:8].[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24](O)=[O:25])[CH:19]=[CH:20][CH:21]=1>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24]([NH:8][CH2:7][CH2:6][N:5]([CH3:4])[C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=2)=[O:25])[CH:... | CN(CCN)c1nccn1C | O=C(O)C#Cc1cccc(Cl)c1 | null | N=C=N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | 2.3 g (≅2.8 mmol) PS carbodiimide was added to a solution of 215 mg (1.4 mmol) N1-methyl-N1-(1-methyl-1H-imidazol-2-yl)ethane-1,2-diamine and 378 mg (2.1 mmol) 3-(3-chloro-phenyl)propiolic acid in DCM (30 ml) and the reaction solution was shaken for 16 h at RT. The resin was subsequently filtered off, washed with DCM a... | CN(CCNC(=O)C#Cc1cccc(Cl)c1)c1nccn1C | null | 57.1 | null |
1,740,858 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([C:20]4[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=4[O:27][CH2:28][CH:29]4[CH2:31][CH2:30]4)[C:14]=3[NH:13][C:12]=2[CH3:32])=[O:10])[CH2:4][CH2:3]1.[C:33](Cl)(=[O:35])[CH3:34]>>[C:33]([N:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9]([C:11]2[C:15... | CC(=O)Cl | Cc1[nH]c2c(-c3cc(F)ccc3OCC3CC3)ncnc2c1C(=O)NC1CCNCC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 4-(2-cyclopropylmethoxy-5-fluoro-phenyl)-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example D.f12) and commercially acetyl chloride the title compound is obtained as colorless solid. | CC(=O)N1CCC(NC(=O)c2c(C)[nH]c3c(-c4cc(F)ccc4OCC4CC4)ncnc23)CC1 | null | null | null |
56,903 | ord_dataset-56a7c92b497c48c59951f153285b4adc | null | 1979-01-01T00:07:00 | true | [O:1]([C:8]([CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11](Cl)=[O:12])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][CH:21]1[C:39](=[O:40])[N:23]2[C:24]([C:36]([OH:38])=[O:37])=[C:25]([CH2:28][S:29][C:30]3[N:34]([CH3:35])[N:33]=[N:32][N:31]=3)[CH2:26][S:27][C@H:22]12.C(N(CC)CC)C.C>ClCCl.C(=O)(O... | O=C(Cl)C(C(=O)Oc1ccccc1)c1ccccc1 | Cn1nnnc1SCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | α-(Phenoxycarbonyl)phenylacetyl chloride (0.02 M) in dichloromethane (50 ml.) was added to 7-amino-3-(1-methyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylic acid (6.56 g., 0.02 M) and triethylamine (6.0 ml.) in dichloromethane (100 ml.). The resulting solution was stirred at room temperature for three hours then th... | Cn1nnnc1SCC1=C(C(=O)O)N2C(=O)C(NC(=O)C(C(=O)Oc3ccccc3)c3ccccc3)[C@H]2SC1 | null | null | null |
1,522,118 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [CH3:1][N:2]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[O:3][CH2:4][CH:5]([OH:7])[CH3:6].[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1.[Cl-].[NH4+]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:14][C:11]([CH3:13])([O:10][C:8](=[O:9])[N:2]([CH3:1])[O:3][CH2:4][CH:5]([CH3:6])[O:7][C:15](=[O:21])[CH2:16][CH2:17][C:18](... | CC(O)CON(C)C(=O)OC(C)(C)C | O=C1CCC(=O)O1 | null | CN(C)c1ccncc1 | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 20 | To a solution of N-methyl-N-boc-(2-hydroxypropyl)hydroxylamine (227 mg, 1.11 mmol) in dichloromethane (4 mL) were added DMAP (41 mg, 0.333 mmol) and succinic anhydride (167 mg, 1.67 mmol). The resulting mixture was stirred for 20 h at room temperature. The reaction mixture was poured into a saturated solution of ammoni... | CC(CON(C)C(=O)OC(C)(C)C)OC(=O)CCC(=O)O | null | 67 | null |
1,069,178 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]1[CH2:22][O:21]1)[N:14]=[CH:13][CH:12]=[C:11]2[O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[O:32])=[C:26]([F:41])[CH:25]=1)#[N:7]>O1CCCC1>[C:6]([C:... | C1CCNC1 | N#Cc1cc2c(Oc3ccc(NC(=O)Nc4ccc(F)cc4)c(F)c3)ccnc2cc1OCC1CO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 50 | null | After adding tetrahydrofuran (1 ml) and pyrrolidine (0.1 ml) to N-[4-(6-cyano-7-oxiranylmethoxyquinolin-4-yloxy)-2-fluorophenyl]-N′-(4-fluorophenyl)urea (100 mg), the mixture was heated at 50° C. for 30 minutes. The reaction solution was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to... | N#Cc1cc2c(Oc3ccc(NC(=O)Nc4ccc(F)cc4)c(F)c3)ccnc2cc1OCC(O)CN1CCCC1 | null | null | null |
712,299 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [C:1]([NH:8][CH2:9][C@H:10]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:11]1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:34].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN... | O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-] | CC(C)(C)OC(=O)NC[C@H]1O[C@H](CO)[C@@H](OCc2ccccc2)[C@@H]1OCc1ccccc1 | null | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 12 | The product from step 5 was dissolved in dry DMF and cooled to 0° C. Pyridinium dichromate (PDC, 4 molar equiv) was added portion wise and the reaction mixture was stirred at room temperature for 12 h. It was then diluted with EtOAc, washed with saturated aqueous CuSO4, brine, dried over anhydrous Na2SO4 and concentrat... | CC(C)(C)OC(=O)NC[C@H]1O[C@H](C(=O)O)[C@@H](OCc2ccccc2)[C@@H]1OCc1ccccc1 | null | 77 | null |
973,679 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][CH2:13][O:14][CH3:15])=[O:2].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:38]([NH2:47])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([CH3:40])[CH3:39].Cl>CN(C=O)C.O>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:47][C:38]([CH3:40])([C:41]2[CH:46]=[CH:4... | COCOc1cc(C(=O)O)ccc1C=O | CC(C)(N)c1ccccc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 4 | 4-Formyl-3-methoxymethoxybenzoic acid (2.57 g, 12.2 mmol) was dissolved in DMF (50 mL), and the solution was added with EDCI (4.68 g, 24.4 mmol), HOBT monohydrate (1.65 g, 12.2 mmol) and cumylamine (4.03 mL, 24.4 mmol), followed by stirring at room temperature for 4 hours. The reaction mixture was added with water (10 ... | COCOc1cc(C(=O)NC(C)(C)c2ccccc2)ccc1C=O | null | 78.1 | null |
21,289 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | [CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2].S(=O)(=O)(O)O>>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[CH2:9][CH3:10])[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]2)[CH3:2] | CCc1ccc(CCCC(=O)O)cc1CC | null | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Alternatively 4-(3',4'-diethylphenyl) butanoic acid (23.3 g; 0.106 mole) maybe cyclised by stirring at 100° C with 80% sulphuric acid (115 ml) for 11/2 hours. After dilution, extraction into ether, and distillation 15.83 g (74%) of the tetralone was obtained. | CCc1cc2c(cc1CC)C(=O)CCC2 | null | null | null |
941,444 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[S:12](Cl)(=[O:14])=[O:13].[OH-].[NH4+:17]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[S:12]([NH2:17])(=[O:14])=[O:13] | [NH4+] | COc1cccc([N+](=O)[O-])c1S(=O)(=O)Cl | null | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-methoxy-6-nitro-benzenesulfonyl chloride (12.8 g, 50.87 mmol) and 25% ammonium hydroxide is swirled at 65° C. on a rotavap. After 15 min the volume of the resulting solution is reduced to half by evaporation of volatiles at reduced pressure. Collecting the precipitate by filtration after cooling gives 2-... | COc1cccc([N+](=O)[O-])c1S(N)(=O)=O | null | null | null |
1,206,920 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Br:1][C:2]1[C:15](=[O:16])[N:14]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.[OH-].[NH4+:23]>O1CCOCC1>[NH2:23][C:7]1[N:8]=[C:9]([CH3:10])[C:4]2[CH:3]=[C:2]([Br:1])[C:15](=[O:16])[N:14]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:5]=2[N:6]=1 | [NH4+] | Cc1nc(S(C)=O)nc2c1cc(Br)c(=O)n2C1CCCC1 | null | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 110 | null | To a solution of 6-bromo-8-cyclopentyl-4-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.80 g, 2.16 mmol) in dioxane (5 mL) was added ammonium hydroxide (30%, 2.6 mL). The mixture was then heated at 110° C. in a sealed tube for 30 minutes. The solution was concentrated in vacuo and extracted with ethyl ace... | Cc1nc(N)nc2c1cc(Br)c(=O)n2C1CCCC1 | null | 93 | null |
1,442,146 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:13][C:14]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:15]=1[C:16](O)=[O:17].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:16](=[O:17])[C:15]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22]... | Nc1c[nH]c2ncc(Br)c(F)c12 | Cc1ccc(F)c(C(=O)O)c1 | null | O=C1OCCN1P(=O)(Cl)N1CCOC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol, Example 1, Step H), 2-fluoro-5-methylbenzoic acid (281 mg, 1.83 mmol), BOP-Cl (465 mg, 1.83 mmol), and triethylamine (0.606 mL, 4.35 mmol) in DCM (5 mL) was processed as described in Example 62, Step A, to provide N-(5-bromo-4-fluoro-1H... | Cc1ccc(F)c(C(=O)Nc2c[nH]c3ncc(Br)c(F)c23)c1 | null | 62.9 | null |
1,181,521 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(C)(C)C.[K+]>CS(C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:22][C:21]1[CH:20]=[CH:19][C:18]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C... | O=[N+]([O-])c1ccccc1F | Nc1ccc(Oc2ccccc2)cc1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The product (2.03 g) is obtained according to the method of stage 1 of Example 4, by using 3.7 mL of 2-fluoro-nitrobenzene and 7.88 g of 4-phenoxyaniline in the presence of 6.36 g of potassium tert-butanolate in 34 mL of DMSO. | O=[N+]([O-])c1ccccc1Nc1ccc(Oc2ccccc2)cc1 | null | null | null |
79,951 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[C:5]=1[N+]([O-])=O)([O-:3])=[O:2].[N+:23]([O-:26])([OH:25])=O>>[N+:23]([C:9]1[C:8]2[C:7](=[O:19])[C:6]3[C:15](=[CH:16][CH:17]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[C:14](=[O:18])[C:13]=2[CH:12]=[CH:11][CH... | O=C1c2ccccc2C(=O)c2c1ccc([N+](=O)[O-])c2[N+](=O)[O-] | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5.00 kg of this dinitroanthraquinone mixture (consisting of 41.2% of 1,5-dinitroanthraquinone, 39.6% of 1,8-dinitroanthraquinone, 8.9% of 1,6-dinitroanthraquinone and 9.5% of 1,7-dinitroanthraquinone) together with 49.04 kg of 97 percent strength by weight nitric acid (molar ratio 45) continuously flow, per hour, onto ... | O=C1c2ccc([N+](=O)[O-])cc2C(=O)c2c1cccc2[N+](=O)[O-] | null | 1.8 | null |
1,401,259 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [OH-].[K+].[C:3](=[N:16][OH:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS(O[C@H:23]1[CH2:27][CH2:26][N:25](OC(C)(C)C)[C:24]1=C=O)(=O)=O.O>CS(C)=O>[NH:25]1[CH2:26][CH2:27][C@@H:23]([O:17][N:16]=[C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]2[CH:9]=[CH:8][CH:7... | ON=C(c1ccccc1)c1ccccc1 | CC(C)(C)ON1CC[C@H](OS(C)(=O)=O)C1=C=O | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a suspension of KOH powder (4.86 g) in DMSO (250 ml) under vigorous stirring, benzophenone oxime (7.86 g) was added. After stirring at RT for 30 min, a solution of N-tert-butoxy-carbonyl-3-(S)-pyrrolidinyl methanesulfonate (10.0 g) in DMSO (70 ml) was added. After 18 h at RT the reaction was poured into iced water (... | c1ccc(C(=NO[C@@H]2CCNC2)c2ccccc2)cc1 | null | null | null |
66,738 | ord_dataset-b5f1497361c94e5fa55257200189a6a4 | null | 1980-01-01T00:06:00 | true | [CH3:1][C:2]([O:4][C:5]1[C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:14]([N:16]([CH2:18][CH3:19])[OH:17])[CH3:15]>CCOCC>[C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([O:17][N:16]([CH2:18][CH3:19])[CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:1] | CCN(O)CC | CC(=O)Oc1ccccc1C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | To 9.1 g (0.0455 mol) of aspirin chloride dissolved in 100 ml of ether was added 8.1 g (0.09 mol) of N,N-diethylhydroxylamine dissolved in 100 ml of ether. The resulting suspension was filtered and the filtrate was diluted with 800 ml of heptane and filtered again. The ether-heptane filtrate was then concentrated in va... | CCN(CC)OC(=O)c1ccccc1OC(C)=O | null | 84 | null |
583,277 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | Cl[C:2]([CH:4]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:3].[CH2:17]([NH2:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN1CCOCC1>C(OCC)(=O)C>[CH:11]1([CH2:10][CH:4]([C:2]([NH:25][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:3])[C:5]... | CCOC(=O)C(CC1CCCCC1)C(=O)Cl | NCCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCOCC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | A mixture of ethyl 2-chlorocarbonyl-3-cyclohexylpropionate (2.65 mmol), phenethylamine (0.376 mL, 3 mmol) and N-methylmorpholine (0.44 mL, 4 mmol) in ethyl acetate (6 mL) was cooled to between −20 and −10° C. and stirred for 15 minutes. The mixture was allowed to warm to room temperature, stirred for approximately 12 h... | CCOC(=O)C(CC1CCCCC1)C(=O)NCCc1ccccc1 | null | 41.7 | null |
437,401 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [NH:1]1[C:10](N)=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[N:4][C:2]1=S>C(O)CC.[Ni]>[N:1]1[CH:10]=[C:9]2[C:5](=[N:6][CH:7]=[N:8]2)[NH:4][CH:2]=1 | Nc1[nH]c(=S)nc2nc[nH]c12 | null | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCO | null | null | null | null | null | null | null | null | null | null | null | null | 4.39 g (11 mmoles) of thioisoguanine and 7.10 g (121 mmoles) of neutral Raney-nickel are refluxed in 50 ml of 1-propanol for 4.5 hours. The nickel was filtered off and the filtrate evaporated to dryress. The residue (3.79 g/93.8%) was dissolved in 20 ml of chloroform and 0.4 ml methanol and filtered through 24 g of sil... | c1nc2cnc[nH]c-2n1 | null | 140.8 | null |
232,614 | ord_dataset-ed79ebfb2fff4cdbbc3a609c8edeac11 | null | 1991-01-01T00:08:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20]([OH:22])=[O:21]>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20]([O... | CC(C)(C)OC(=O)NCCCCC(=O)O | Nc1cc(C(=O)O)ccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | For the preparation of the starting material, 5-[1-(t-butoxy)formamido]valeric acid and 3-amino-4-chlorobenzoic acid are coupled to give 3-[5-(1-t-butoxyformamido)valeramido]-4-chlorobenzoic acid, m.p. 203° C., and the latter is coupled with β-alanine t-butyl ester to give N-[3-[5-(1-t-butoxyformamido)valeramido]-4-chl... | CC(C)(C)OC(=O)NCCCCC(=O)Nc1cc(C(=O)O)ccc1Cl | null | null | null |
1,543,721 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][OH:18])=[N:15][O:14][N:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].N1C(C)=CC=CC=1C.O([Si:35]([CH:42]([CH3:44])[CH3:43])([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])S(C(F)(F)F)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][O:18][... | O=C(Nc1ccc(F)c(Cl)c1)c1nonc1CO | CC(C)[Si](OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1cccc(C)n1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a stirred solution of N-(3-chloro-4-fluorophenyl)-4-(hydroxymethyl)-1,2,5-oxadiazole-3-carboxamide (3.2 g, 0.012 mol) in dichloromethane (DCM) (23 mL) at 0° C. was added 2,6-lutidine (3.4 mL, 0.029 mol) followed by triisopropylsilyl triflate (4.1 mL). The solution was stirred at 0° C. for 30 min and then the reactio... | CC(C)[Si](OCc1nonc1C(=O)Nc1ccc(F)c(Cl)c1)(C(C)C)C(C)C | null | 91 | null |
1,049,363 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | CO[C:3](=[O:38])[N:4]=[C:5](SC)[C:6]([C:20]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[C:22]([O:28][CH2:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])[C:21]=1[F:35])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.Cl.[NH:40]([C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44]([... | NNc1ccccc1C(=O)O | CCc1cc(OCC(=O)N(C)C)c(F)c(C(=Nc2ccc(-c3noc(C)n3)cc2)C(=NC(=O)OC)SC)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The same procedure was carried out as in Example (2f), except that 0.409 g of {2-(3-dimethylcarbamoylmethoxy-5-ethyl-2-fluorophenyl)-2-[4-(5-methyl -[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester was used instead of the [2-(4-cyanophenylimino)-2-(2-fluoro-3,5-dimethoxyphenyl)-1... | CCc1cc(OCC(=O)N(C)C)c(F)c(C(Nc2ccc(-c3noc(C)n3)cc2)c2nn(-c3ccccc3C(=O)O)c(=O)[nH]2)c1 | null | 60.2 | null |
402,681 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:19](=[O:20])[C:18](=[O:21])[C:17]=3[O:22]CC)[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH2:30][CH:29]1[C:41]([NH2:43])=[O:42])=[O:27].[OH-].[Na+]>C(... | CCOc1c(N2CCC(Oc3ccc(CC(=O)N4CCN(c5ccccc5C)CC4C(N)=O)c(OC)c3)CC2)c(=O)c1=O | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 1-(2-Methoxy-4-(1-(3-ethoxy-3-cyclobutene-1,2-dion-4-yl)-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide (87 mg, 0.147 mmole) was dissolved in 3 ml of ethanol, treated with one equivalent of 1N sodium hydroxide solution, and stirred at ambient temperature overnight. All volatiles were removed un... | COc1cc(OC2CCN(c3c(O)c(=O)c3=O)CC2)ccc1CC(=O)N1CCN(c2ccccc2C)CC1C(N)=O | null | null | null |
1,764,433 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][N:2]1[CH:7]=[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)[N:5]=[C:4]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30]C(=O)OC(C)(C)C)[CH2:25]2)[C:3]1=[O:38]>C(O)(C(F)(F)F)=O.ClCCl>[NH2:30][C@H:26]1[CH2:27][CH2:28][CH2:29][N:24]([C:4]2... | Cc1cncc(-c2cc3c(cn2)cnn3-c2cn(C)c(=O)c(N3CCC[C@H](NC(=O)OC(C)(C)C)C3)n2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of tert-butyl N-[(3S)-1-[4-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-3-oxo-pyrazin-2-yl]-3-piperidyl]carbamate (0.3505 mmol; 181.4 mg) in TFA (1 mL) and dichloromethane (4 ml) was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse p... | Cc1cncc(-c2cc3c(cn2)cnn3-c2cn(C)c(=O)c(N3CCC[C@H](N)C3)n2)n1 | null | 19.2 | null |
1,058,460 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]2[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=2)=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:1][... | CCCCCCNc1ccc(F)c(C(=O)OC)c1 | O=Cc1ccc(C#Cc2ccc(F)cc2)cc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | 50 | null | To a solution of methyl 2-fluoro-5-(hexylamino)benzoate (270 mg; 1.07 mmol) and 4-[(4-fluorophenyl)ethynyl]benzaldehyde (358 mg; 1.60 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) in anhydrous DCE (15 mL) was added sodium triacetoxyborohydride (678 mg; 3.20 mmol) at rt. The re... | CCCCCCN(Cc1ccc(C#Cc2ccc(F)cc2)cc1)c1ccc(F)c(C(=O)OC)c1 | null | 32 | null |
1,275,907 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:6]([OH:8])=O)=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:35]([C:37]1[CH:38]=[C:39]([CH:44]=[C:45]([CH3:48])[C:46]=1[OH:47])[C:40]([NH:42]O)=[NH:41])[CH3:36]>CN(C=O)C>[CH2:35]([C:37]1[CH:38]=[C:39]([C:40]2[N:41]=[C:6]([C:5]3[CH:4]=[C:3]([CH:11]=[C:10]... | CCc1cc(C(=N)NO)cc(C)c1O | Cc1cc(C=O)cc(C(=O)O)c1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of 3-formyl-5-methyl-benzoic acid (3.80 g, 23.2 mmol), HOBt (4.17 g, 27.8 mmol) and EDC HCl (4.44 g, 23.2 mmol) in DMF (200 mL) was stirred at rt for 5 min before 3-ethyl-4,N-dihydroxy-5-methyl-benzamidine (4.50 g, 23.2 mmol) was added. The mixture was stirred at rt for 1 h. The mixture was heated to 75° C. ... | CCc1cc(-c2noc(-c3cc(C)cc(C=O)c3)n2)cc(C)c1O | null | 28.6 | null |
1,760,991 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10]2([C:13]([OH:15])=O)[CH2:12][CH2:11]2)=[CH:4][C:3]=1[CH3:16].[O-:17][C:18]#[N:19].[K+].C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCl>[Br:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([N:9]2[C:18](=[O:17])[NH:19][C:13](=[O:15])[C:10]32[CH2:11][CH2:12]3)=[CH:6][C:7]=1[CH3:8] | Cc1cc(NC2(C(=O)O)CC2)cc(C)c1Br | N#C[O-] | null | O=C([O-])O | [K+] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | To a mixture of 1-((4-bromo-3,5-dimethylphenyl)amino)cyclopropane carboxylic acid (198 mg, 0.697 mmol) in acetic acid (3 mL) and dichloromethane (1.5 mL), potassium cyanate (424 mg, 5.23 mmol) was added at room temperature. The mixture was stirred at room temperature for one hour, and then stirred at 60° C. for two hou... | Cc1cc(N2C(=O)NC(=O)C23CC3)cc(C)c1Br | null | 22.7 | null |
970,777 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)#[CH:9] | C[Si](C)(C)C#Cc1ccc(I)cc1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 48 | To a solution of ((4-iodophenyl)ethynyl)trimethylsilane (5) (2.07 g, 6.23 mmol) in methanol (40 mL) was added K2CO3 (8.0 g, 57.9 mmol) and the reaction was allowed to stir for 48 hours. The volatiles were then removed in vacuo and the residue partitioned between ethyl acetate and H2O. The layers were separated and the ... | C#Cc1ccc(I)cc1 | null | 64.8 | null |
176,172 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | [N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][N:22]1C(=O)C2=CC=CC=C2C1=O>CN(C)C=O>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])[CH2:6][CH2:5][CH2:4][CH2:3]... | Oc1cccc(CN2CCCCC2)c1 | O=C1c2ccccc2C(=O)N1CCCCBr | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 3 | A mixture of 3-(1-piperidinylmethyl)phenol (8.7 g) and sodium hydride (1.2 g) in dimethylformamide (60 ml) was stirred at 25° during 3 h. N-(4-Bromobutyl)phthalimide (12.8 g) was added and the mixture was stirred at 25° during 20 h then at 65° for 3 h. The reaction mixture was poured onto water and extracted with ethyl... | NCCCCOc1cccc(CN2CCCCC2)c1 | null | 34.4 | null |
450,781 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | CN1CCCC1=O.[NH2:8][C:9]1[C:14]([F:15])=[CH:13][N:12]=[C:11](F)[CH:10]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[CH2:17]([NH:24][C:11]1[CH:10]=[C:9]([NH2:8])[C:14]([F:15])=[CH:13][N:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1 | Nc1cc(F)ncc1F | NCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | null | To 1 ml of N-methylpyrrolidone was added 410 mg of 4-amino-2,5-difluoropyridine together with 930 mg of benzylamine, and the mixture was allowed to react in nitrogen atmosphere at 150° C. for 3 days and allowed to cool. After adding 30 ml of chloroform, the mixture was washed twice with 300 ml of distilled water. The c... | Nc1cc(NCc2ccccc2)ncc1F | null | 58.4 | null |
786,524 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](I)[CH:11]=1)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O-:19])=[O:18])=[CH:5]2.[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2... | OB(O)c1ccc(F)cc1 | O=C([O-])C1=Cc2cc(Cl)cc(I)c2OC1C(F)(F)F | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 | null | To 0.400 g (0.428 mmole) of Wang resin 6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 50 mg (0.043 mmole) tetrakis(triphenylphosphine)palladium(0), 0.180 g (1.285 mmole) 4-fluorophenylboronic acid, 0.857 mL K2CO3 (2M soln degassed), and 4 mL degassed DMF. The reaction mixture was heated to 100°... | O=C(O)C1=Cc2cc(Cl)cc(-c3ccc(F)cc3)c2OC1C(F)(F)F | null | 34 | null |
1,392,016 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]1[O:14][C@@H:13]1[CH2:15]Cl>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:15][C@H:13]2[CH2:12][O:14]2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3] | ClC[C@@H]1CO1 | CC(C)(C)c1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 4-tert-butyl-phenol and S-epichlorohydrin employing the procedures as set forth in Step 1 of Example 1. | CC(C)(C)c1ccc(OC[C@H]2CO2)cc1 | null | null | null |
119,286 | ord_dataset-9625b7c45a574cd58946dd2c1803eb6f | null | 1984-01-01T00:07:00 | true | [CH2:1]([CH:3]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]1O)[CH3:2].[H][H]>[Ni]>[CH2:17]([CH:12]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][CH:7]1[CH2:8][CH2:9][CH2:10][CH:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:20][CH... | [H][H] | CCCCC(CC)CC1CCCC(CC(CC)CCCC)C1O | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 300 Grams of 2,6-di(2-ethylhexyl)-cyclohexanol were hydrogenated with 30 gm of Girdler nickel 49A for six hours at 250° C. and 250 bar of hydrogen pressure. After filtration of the catalyst, 260 gm of 1,3-di-(2-ethylhexyl)-cyclohexane remained with the following characteristics: | CCCCC(CC)CC1CCCC(CC(CC)CCCC)C1 | null | null | null |
1,322,472 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Br[C:2]1[N:7]2[C:8]([NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[O-:25][CH2:26][CH3:27].[Na+]>>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:25][CH2:26][CH3:2... | Clc1ccccc1-c1nc2cccc(Br)n2c1NC1CCCCC1 | CC[O-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine 42 (152 mg, 0.376 mmol) was added to sodium ethoxide [generated in situ by addition of sodium metal (17.32 mg) to absolute ethanol (10 ml)]. The mixture was heated under reflux for 8 h. Excess solvent was removed in vacuo and the resultant mixture was... | CCOc1cccc2nc(-c3ccccc3Cl)c(NC3CCCCC3)n12 | null | null | null |
1,269,038 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][N:19]=[C:18]4[CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][... | CCCN(CC1CC1)c1cc(C(=O)Nc2ccc3[nH]nc(CCC(=O)OC)c3c2)ncn1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of methyl 3-{5-[({6-[(cyclopropylmethyl)(propyl)amino]pyrimidin-4-yl}carbonyl)amino]-1H-indazol-3-yl}propanoate (Example 123, 20 mg; 0.05 mmol) in ethanol (1 ml) was treated with 10% sodium hydroxide solution (1 ml). After stirring at RT for 2 hours the mixture was acidified to pH 3 with dilute HCl and extra... | CCCN(CC1CC1)c1cc(C(=O)Nc2ccc3[nH]nc(CCC(=O)O)c3c2)ncn1 | null | null | null |
1,060,233 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [F:1][C:2]([F:18])([F:17])[CH2:3][C:4](=O)[CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C([O-])(=O)C.[NH4+:23]>C(O)C>[NH2:23]/[C:4](/[CH2:3][C:2]([F:18])([F:17])[F:1])=[CH:5]/[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7] | O=C(CC(=O)OCc1ccccc1)CC(F)(F)F | [NH4+] | null | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | null | Benzyl 5,5,5-trifluoro-3-oxopentanoate (2.1 g) in ethanol (15 mL) was treated with ammonium acetate (2 g). The mixture was heated at 80° C. for 18 h and was then concentrated in vacuo. Water and DCM were added. The organic phase was separated and washed with sodium bicarbonate solution and water and then dried over sod... | N/C(=C/C(=O)OCc1ccccc1)CC(F)(F)F | null | 33.9 | null |
1,489,077 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [NH2:1][CH:2]1[CH:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][CH2:19][CH2:20][NH:21][S:22]([C:25]3[N:26]=[CH:27][N:28]([CH3:30])[CH:29]=3)(=[O:24])=[O:23])[CH:8]=2)[CH2:3]1.C(NC(C)C)(C)C.[Cl:38][CH2:39][C:40]([CH3:45])([CH3:44])[C:41](Cl)=[O:42].Cl>ClCCl>[CH2:11]([C... | CC(C)(CCl)C(=O)Cl | Cn1cnc(S(=O)(=O)NCCOc2ccc3c(c2)C(Cc2ccccc2)C(N)C3)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(C)NC(C)C | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of N-(2-(2-amino-3-benzyl-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (40.5 mg, 0.095 mmol; see example 193) in dry dichloromethane (2 ml) containing diisoproylamine (0.025 ml, 0.142 mmol) and under argon was added a solution of 3-chloropivaloyl chloride (0.019 ml, 0.142 mmol) ... | Cn1cnc(S(=O)(=O)NCCOc2ccc3c(c2)C(Cc2ccccc2)C(NC(=O)C(C)(C)CCl)C3)c1 | null | null | null |
548,927 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:5]2.[Mg]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[CH2:5]2 | COC(=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 8 | Methyl 5-chloroindole-2-carboxylate (0.6 g, 2.87 mmol) and magnesium shavings (0.34 g, 14.3 mmol) were suspended in methanol (40 ml) and the mixture was stirred for 8 h. The mixture was filtered, treated with methylene chloride (100 ml) and washed with NH4Cl solution. The organic fraction was dried (Na2SO4) and the sol... | COC(=O)C1Cc2cc(Cl)ccc2N1 | null | null | null |
217,126 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | Cl[CH2:2][C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]2[N:21]=[CH:22][C:23]([C:24]#[N:25])=[C:6]12)=[O:4].[F:26][C:27]([F:42])([F:41])[C:28]1[CH:40]=[CH:39][CH:38]=[CH:37][C:29]=1[CH2:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].... | FC(F)(F)c1ccccc1CN1CCNCC1 | N#Cc1cnn2c1N(C(=O)CCl)CC=C2c1cccc(C(F)(F)F)c1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 7.4 g of 4-(chloroacetyl)-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile, 5.4 g of 2-trifluoromethylbenzyl piperazine and 2.4 g of sodium carbonate in 260 ml of toluene was reacted as described in Example 146, giving 6.1 g of the desired product, mp 169°-171° C. | N#Cc1cnn2c1N(C(=O)CN1CCN(Cc3ccccc3C(F)(F)F)CC1)CC=C2c1cccc(C(F)(F)F)c1 | null | 52.6 | null |
1,440,114 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:12])[N:3]=1.C(=O)(O)[O-].[Na+].Cl[CH2:19][CH:20]=O>CO.O>[Cl:12][C:4]1[N:3]2[CH:19]=[CH:20][N:1]=[C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1 | COC(=O)c1ccc(Cl)nc1N | O=CCCl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | 16 | To a stirred suspension of methyl 2-amino-6-chloro-3-pyridinecarboxylate (2 g, 10.72 mmol) and sodium bicarbonate (900 mg, 10.72 mmol) in a mixture of methanol (40 mL) and water (20 mL) was added chloroacetaldehyde (50% wt. solution in water, 2.9 mL, 22.51 mmol). The resultant mixture was heated at reflux for 5 hours w... | COC(=O)c1ccc(Cl)n2ccnc12 | null | 58.5 | null |
780,196 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [OH:1][C@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([O:17][C:18]2[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=2)[CH:11]=1>>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[C@@H:2]([O:1][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:12]3[CH:13]=[CH:14][C:15]([OH:16])=[CH:10][CH:... | Oc1ccc(Oc2ccc(O)cc2)cc1 | O[C@@H]1CN2CCC1CC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-(S)-Hydroxy-quinuclidine (the product of Reference Example 2D, 127 mg, 1 mmol) was treated with 4,4′-dihydroxydiphenyl ether (TCl, 202 mg, 1 mmol) according to the procedure of Example 1A. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.2) as oil (48 mg, yield, 15%). 1H NM... | Oc1ccc(Oc2ccc(O[C@H]3CN4CCC3CC4)cc2)cc1 | null | null | null |
1,367,717 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[C:8](=O)[CH2:7][CH:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:5][C:4]=2[N:3]=1.NC1N=C(C)C2C(=[N:38][OH:39])CC(C3C=CC=CC=3C3C=CC=CC=3)CC=2N=1>>[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[C:8](=[N:38][OH:39])[CH2:7][CH:6]([C... | Cc1nc(N)nc2c1C(=NO)CC(c1ccccc1-c1ccccc1)C2 | Cc1nc(N)nc2c1C(=O)CC(c1ccccc1-c1ccccn1)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-amino-4-methyl-7-(2-pyridin-2-yl-phenyl)-7,8-dihydro-6H-quinazolin-5-one from stage 1, following the procedure describing the synthesis of 2-amino-7-biphenyl-2-yl-4-methyl-7,8-dihydro-6H-quinazolin-5-one oxime (example 5/a stage 2—method A). | Cc1nc(N)nc2c1C(=NO)CC(c1ccccc1-c1ccccn1)C2 | null | null | null |
6,012 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | C[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH:17]=[C:18]([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:3]([OH:5])=[O:4].C(O)C.[OH-].[K+]>O>[CH3:24][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH2:16][CH:15]=[CH:14][CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][... | CCCCCC(C)=CCC=CCC=CCCCCCC(C)C(=O)O | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1.3 g. of methyl 15-methyl-8,11,14-eicosatrienoic acid, 12.8 ml of 95% ethanol, 1.1 g. of potassium hydroxide and 1.1 ml. of water under a nitrogen atmosphere was heated under reflux for 2hours, then water and Skellysolve "B" (mixed hexanes) were added. The aqueous and organic layers were separated and the... | CCCCCC(C)=CCC=CCC=CCCCCCCC(=O)O | null | null | null |
1,218,732 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:19])[C:10]2[CH:11]=[CH:12][C:13]([F:18])=[C:14]([CH:17]=2)[C:15]#[N:16])[CH:5]=[C:6]([F:8])[CH:7]=1.O.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[C:9]([C:10]1[CH:11]=[CH:12][C:13]([F:18])=[C:14]([CH:17]=1)[C... | N#Cc1cc(C(O)c2cc(F)cc(F)c2)ccc1F | null | null | O=[Ru](=O)(=O)[O-] | CCC[N+](CCC)(CCC)CCC | C[N+]1([O-])CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of 5-[(3,5-Difluoro-phenyl)-hydroxy-methyl]-2-fluoro-benzonitrile (2.68 g, 10.2 mmol), 4-methylmorpholine N-oxide monohydrate (2.02 g, 15 mmol) and tetrapropylammonium perruthenate (35 mg, 0.1 mmol) in dry dichloromethane (50 mL) was stirred at room temperature for 2 hours. The reaction mixture was evaporated... | N#Cc1cc(C(=O)c2cc(F)cc(F)c2)ccc1F | null | 76.9 | null |
990,532 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[CH:10][C:5]=2[N:4]=[CH:3]1>CCO.[Pd]>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[N:4]=[CH:3]1 | Cn1cnc2cc([N+](=O)[O-])ccc21 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 18 | 1-Methyl-5-nitro-1H-benzo[d]imidazole (prepared as described in WO 2005/092899; 1.14 g, 6.43 mmol) in EtOH (50 ml) was stirred under H2 (1 atm) at RT in the presence of 10% Pd/C (50 wt % H2O, 1.37 g, 0.643 mmol). After 18 h, the completed reaction was filtered on Celite, rinsing forward with EtOH. The combined filtrate... | Cn1cnc2cc(N)ccc21 | null | 107.8 | null |
1,434,429 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.N1C=CC=CC=1.[C:16](Cl)(=[O:18])[CH3:17]>ClCCl>[C:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9])(=[O:18])[CH3:17] | Cc1cc(Br)ccc1O | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 0 | 2 | An ice-cold solution of 4-bromo-2-methylphenol (5.6 g, 30 mmol) and pyridine (6.1 mL, 75 mmol) in 50 mL of anhydrous dichloromethane was treated with a solution of acetyl chloride (2.8 mL, 26 mmol) in 5 mL of anhydrous dichloromethane. After 2 hours, the reaction mixture was concentrated in vacuo. The resulting residue... | CC(=O)Oc1ccc(Br)cc1C | null | 115.9 | null |
763,020 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([NH:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20]... | CCOC(=O)C(=CNc1cc(N)nc(SC)n1)C(=O)OCC | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 16 | A mixture of EXAMPLE 16A (9.91 g) and acetic anhydride (150 mL) at reflux was stirred for 16 hours, treated with additional acetic anhydride (60 mL), refluxed for 5 hours, cooled and concentrated. The concentrate was dissolved in 9:1 ethanol/ethyl acetate (100 mL), stored at 0° C. for 18 hours, and filtered. 1H NMR (30... | CCOC(=O)C(=CNc1cc(NC(C)=O)nc(SC)n1)C(=O)OCC | null | null | null |
14,839 | ord_dataset-b971427c0b944c56b63bb2356fa8ca69 | null | 1976-01-01T00:11:00 | true | CO[C:3]([CH:5]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:9]=2[N:8]([CH3:18])[C:7](=[O:19])[CH2:6]1)=[O:4].[NH2:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1>C1(C)C=CC=CC=1>[Cl:17][C:15]1[CH:14]=[CH:13][C:10]2[C:11](=[O:12])[CH:5]([C:3](=[O:4])[NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)[CH2:6][C:7](=[O:1... | COC(=O)C1CC(=O)N(C)c2cc(Cl)ccc2C1=O | Nc1nccs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | The mixture of 23.0 g of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1-benzazepine-2,5-dione-4-carboxylic acid methyl ester, 8.9 g of 2-aminothiazole and 360 ml of toluene is distilled for 20 hours so that after collecting 100 ml of toluene each, this amount is returned to the reaction mixture. It is finally concentrated to a... | CN1C(=O)CC(C(=O)Nc2nccs2)C(=O)c2ccc(Cl)cc21 | null | null | null |
401,535 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [CH3:1][NH:2][NH2:3].[C:4]([C:9]1[C:13]([Cl:14])=[C:12]([Cl:15])[NH:11][C:10]=1[CH:16]=O)(OCC)=[O:5].S(=O)(=O)(O)O>C(O)C>[Cl:15][C:12]1[NH:11][C:10]2[CH:16]=[N:3][N:2]([CH3:1])[C:4](=[O:5])[C:9]=2[C:13]=1[Cl:14] | CNN | CCOC(=O)c1c(C=O)[nH]c(Cl)c1Cl | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of methylhydrazine (4.72 g) and 3-carbethoxy-4,5-dichloro-2-formylpyrrole (4.72 g) in ethanol (50 ml) was refluxed for 2 hours. After cooling to room temperature, concentrated sulfuric acid (0.5 ml) was added and the mixture was refluxed for another 21 hours. The reaction mixture was cooled to room temperatu... | Cn1ncc2[nH]c(Cl)c(Cl)c2c1=O | null | 75.5 | null |
915,437 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH:11]=[O:12])[NH:8][C:7]=12.[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOCC.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[OH:12])[NH:8][C:7]=12 | O=Cc1cc2ccnc(Cl)c2[nH]1 | Br[Mg]c1ccccc1 | null | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 138) (1.0 g, 5.5 mmol) in THF (27.7 mL) was added 3.0 M phenylmagnesium bromide in Et2O (3.8 mL, 11.3 mmol) at −78° C. under a nitrogen atmosphere. After stirring for ca. 2 h, additional 3.0 M phenylmagnesium bromide in Et2O (0.92 mL, 2.7 mmo... | OC(c1ccccc1)c1cc2ccnc(Cl)c2[nH]1 | null | 67 | null |
1,544,827 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [OH:1][C:2]1[C:3](=[O:20])[CH:4]=[C:5]([CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])(=[O:12])=[O:11])[O:6][CH:7]=1.[OH:21][C:22]1C(=O)C=C(CNS(C2C=CC=CC=2)(=O)=O)OC=1CO>>[OH:1][C:2]1[C:3](=[O:20])[CH:4]=[C:5]([CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])(=[O:12])... | Cc1ccccc1S(=O)(=O)NCc1cc(=O)c(O)co1 | O=c1cc(CNS(=O)(=O)c2ccccc2)oc(CO)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | N-(5-Hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-2-methyl-benzenesulfonamide (9-02) (9.0 g, 62.78%) was synthesized as a white solid from N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-2-methyl-benzenesulfonamide (8-02) (13.0 g, 44.06 mmol) following the procedure described for N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyr... | Cc1ccccc1S(=O)(=O)NCc1cc(=O)c(O)c(CO)o1 | null | 62.78 | null |
1,249,808 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([CH:15]3[CH:19]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=4[CH3:27])[C:18]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[F:37])([C:28]#[N:29])[CH:17]([CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[NH:16]3)=[O:14])=[CH:8][CH:7]=2)=[N:4][N:3]=[N:2]1.[C:... | O=C([O-])O | Cc1c(Cl)cccc1C1C(C(=O)Nc2ccc(-c3nnn[nH]3)cc2)NC(CC(C)(C)C)C1(C#N)c1ccc(Cl)cc1F | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | COS(=O)(=O)OC | null | null | null | null | null | null | null | null | null | 25 | 5 | To a stirred solution of rac (2R,3R,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-methyl-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [4-(1H-tetrazol-5-yl)-phenyl]-amide (32 mg, 0.0524 mmol) in acetone (5 mL), sodium bicarbonate (45 mg, 0.6 mmol) and dimethyl sulfate (0.11 mmol) was added a... | Cc1c(Cl)cccc1C1C(C(=O)Nc2ccc(-c3nnnn3C)cc2)NC(CC(C)(C)C)C1(C#N)c1ccc(Cl)cc1F | null | 9.2 | null |
969,700 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Br:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]([C:10]#[N:11])=[C:6]([CH3:9])[C:7]=1I.[N+:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=... | COc1c(Br)c(I)c(C)c(C#N)c1NC(=O)C(C)(C)C | O=[N+]([O-])c1cccc(B(O)O)c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=P([O-])([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 95 | 4 | N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide (I-6) (965 mg, 2.14 mmol), 3-nitrophenylboronic acid (375 mg, 2.25 mmol), tripotassium phosphate (74-85%, 1.23 g, 4.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (247 mg, 0.214 mmol) were added to a 50-ml eggplant-type flask, followed ... | COc1c(Br)c(-c2cccc([N+](=O)[O-])c2)c(C)c(C#N)c1NC(=O)C(C)(C)C | null | 67.5 | null |
1,288,973 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[C:31](Cl)[N:30]=[N:29][C:28]=2[CH2:34][CH2:35][CH2:36][CH3:37])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1COCC1>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][... | CCCCc1nnc(Cl)cc1-c1ccc(OCc2ccccc2)cc1 | OCCCN1CCCCC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.17 | To a stirred solution of 3-piperidin-1-yl-propan-1-ol (0.85 mmol, 121 mg) in THF at room temperature, NaH (1.2 mmol, 29 mg) was added and stirring continued for 10 min then 4-(4-benzyloxy-phenyl)-3-butyl-6-chloro-pyridazine (Example 1, 0.42 mmol, 150 mg) was added. The resulting mixture was stirred at 50-55° C. over ni... | CCCCc1nnc(OCCCN2CCCCC2)cc1-c1ccc(OCc2ccccc2)cc1 | null | null | null |
936,130 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [CH:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=3)[C:12]([C:22]3[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH:27]=3)=[CH:11]2)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[NH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([S:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH... | CN1CC=C(c2cn(S(=O)(=O)C3CCCCC3)c3ccc([N+](=O)[O-])cc23)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 20 | 200 mg of 50% Pd/C with a humidity of 5% were added to a solution of 403 mg (1 mMol) of 1-cyclohexanesulfonyl-3-(1-methyl-1,2,3,6-tetrahydropyridine-4-yl)-5-nitro-1H-indole in 200 ml of ethanol. The resulting suspension was hydrogenized at 25 psi of overpressure for 20 hours. Then the catalyst was filtered and evaporat... | CN1CC=C(c2cn(S(=O)(=O)C3CCCCC3)c3ccc(N)cc23)CC1 | null | 40.2 | null |
1,658,831 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:4]=2[O:3]1.[F:27][CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][N:12]([C:13]3[CH:1... | O=C(Cl)CF | CC1(C)Cc2cccc(CNc3ccccc3Oc3ccccc3)c2O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 1 | To a solution of N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-N-(2-phenoxy phenyl)amine (0.20 g, 0.58 mmol) dissolved in DCM (2 mL) was added TEA (0.24 g, 2.32 mmol, 0.32 mL). The reaction was cooled to 0° C. and fluoroacetyl chloride (0.11 g, 1.16 mmol, 0.08 mL) was added. The mixture was stirred at room tempera... | CC1(C)Cc2cccc(CN(C(=O)CF)c3ccccc3Oc3ccccc3)c2O1 | null | 72.3 | null |
112,017 | ord_dataset-5237a168f9214b7ca3db5a1dc3e62d07 | null | 1983-01-01T00:12:00 | true | [OH-].[Ca+2].[OH-].Cl.[C:5]([OH:17])(=[O:16])[CH:6]([CH:8]([CH2:12][C:13]([OH:15])=[O:14])[C:9]([OH:11])=[O:10])O>O>[CH2:12]([C:13]([OH:15])=[O:14])/[C:8](/[C:9]([OH:11])=[O:10])=[CH:6]\[C:5]([OH:17])=[O:16] | O=C(O)CC(C(=O)O)C(O)C(=O)O | null | null | Cl | [Ca+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 75 | 2 | Thirty one grams (0.1 mole) of product prepared as in Example I-B is mixed with 200 mls water. Thirty grams (0.4 mole) calcium hydroxide is added slowly while the pH of the reaction medium is maintained at 10-10.5 and the temperature is kept between 70° and 75° C. After the addition of calcium hydroxide is complete, th... | O=C(O)/C=C(\CC(=O)O)C(=O)O | null | 60 | null |
285,111 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH2:13][NH:14][C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH:10]([OH:12])[CH3:11])=[O:6])[CH:2]=[CH2:3].N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C)C=O.C(OCC)(=O)C>[CH2:18]([O:17][C:15]([NH:14][CH2:13][CH:9]([CH2:8][NH:7][C:5]([O:4][CH2:1][... | CC(C)(C)[Si](C)(C)Cl | C=CCOC(=O)NCC(CNC(=O)OCC=C)C(C)O | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 14 | To a stirred solution of 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)butan-3-ol (90.00 g) in N,N-dimethylformamide (800 ml) were added imidazole (85.51 g) and t-butyldimethylsilyl chloride (61.53 g). The resulting mixture was allowed to stand at ambient temperature for 14 hours. The mixture was diluted wit... | C=CCOC(=O)NCC(CNC(=O)OCC=C)C(C)O[Si](C)(C)C(C)(C)C | null | 91.6 | null |
1,686,650 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].C(O[Cl:15])(C)(C)C>CO>[Cl:15][N:6]1[CH2:7][CH2:8][N:4]([CH2:3][CH2:2][OH:1])[C:5]1=[O:9] | CC(C)(C)OCl | O=C1NCCN1CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 1.5 | A solution of 1-(2-hydroxyethyl)imidazolidin-2-one (418 mg, 3.2 mmol) in MeOH (6 ml) was cooled to 0° C. tert-Butylhypochlorite (450 ul, 4 mmol) was added. The resulting solution was stirred for 90 min and then concentrated under reduced pressure. The crude material was purified by column chromatography (0 to 12% metha... | O=C1N(Cl)CCN1CCO | null | 60.3 | null |
1,062,074 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[C:8](B(O)O)=[CH:7][CH:6]=[CH:5][N:4]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([C@H:19]([N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])[CH3:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=C... | COc1ncccc1B(O)O | C[C@H](c1ccc(Br)cc1)N1C(=O)c2ccccc2C1=O | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 150 | null | A mixture of (R)-1-(4-bromophenyl)ethylamine (3.12 g, 15.6 mmol), pthalic anhydride (2.31 g, 15.6 mmol) and dimethylformamide (20 ml) was heated in a microwave oven at 210° C. for 20 min. The reaction mixture was then partitioned between diethyl ether and water, and the organic phase washed with brine. The solvent was ... | COc1ncccc1-c1ccc([C@@H](C)N2C(=O)c3ccccc3C2=O)cc1 | null | 44.8 | null |
1,009,059 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[C... | O=Cc1ccccc1C(F)(F)F | NCCCCNC(=O)c1ccc(CN(Cc2ncc[nH]2)Cc2ncc[nH]2)cc1 | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(OC)OC | CO | null | null | null | null | null | null | null | null | null | 25 | 0.5 | The compound (50.6 mg) obtained in Example 3-2 was dissolved in anhydrous methanol (2.0 ml) and added with 2-trifluoromethylbenzaldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (0.0260 ml) and trimethyl orthoformate (0.0430 ml), followed by stirring at room temperature for 30 minutes. Then, the solution was added... | O=C(NCCCCNCc1ccccc1C(F)(F)F)c1ccc(CN(Cc2ncc[nH]2)Cc2ncc[nH]2)cc1 | null | null | null |
704,467 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26]([F:29])([F:28])[F:27])=[N:25][C:20]2=[N:19][CH:18]=1)CCC>>[F:28][C:26]([F:27])([F:29])[C:24]1[CH:23]=[CH:22][N:21]2[C:17]([C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=3)=... | CCCC[Sn](CCCC)(CCCC)c1cnc2nc(C(F)(F)F)ccn12 | FC(F)(F)c1cccc(Cl)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-Chloro-6-trifluoromethylpyridine (385 mg, 2.1 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.4 mmol) by the method of Example 1 to give 7-trifluoromethyl-3-(6-trifluoromethyl-pyridin-2-yl)imidazo[1,2-α]pyrimidine (65 mg) as a white solid: δH (360 MHz, DMSO) 7.89 (2H, d, J 7.4), 8.... | FC(F)(F)c1cccc(-c2cnc3nc(C(F)(F)F)ccn23)n1 | null | 14 | null |
1,719,873 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH2:18][N:19]([C:27]2[N:35]=[CH:34][N:33]=[C:32]3[C:28]=2[N:29]=[CH:30][N:31]3C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C(=O)OC(C)(C)C)[O:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:35]1[C:27]([NH:19][CH2:18][C:4]2[O:3]... | CC(C)(C)OC(=O)N(Cc1oc(=O)c2ccccc2c1-c1ccccc1)c1ncnc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | tert-Butyl (1-oxo-4-phenyl-1H-isochromen-3-yl)methyl(9-trityl-9H-purin-6-yl)carbamate (80 mg, 0.112 mmol) was dissolved in DCM (0.7 ml) and TFA (1 mL) at RT for 45 min. Solvent was then removed and the crude was straightforward purified by Preparative HPLC (method 1) to the title compound (17 mg, 40.9%). | O=c1oc(CNc2ncnc3[nH]cnc23)c(-c2ccccc2)c2ccccc12 | null | null | null |
296,452 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | [CH:1]([Si:3]([CH:8]=[CH2:9])([CH:6]=[CH2:7])[CH:4]=[CH2:5])=[CH2:2].[CH3:10][SiH:11]([CH3:16])[O:12][SiH:13]([CH3:15])[CH3:14]>>[CH:1]([Si:3]([CH:8]=[CH2:9])([CH:6]=[CH2:7])[CH2:4][CH2:5][Si:11]([CH3:16])([CH3:10])[O:12][Si:13]([CH2:9][CH2:8][Si:3]([CH:6]=[CH2:7])([CH:4]=[CH2:5])[CH:1]=[CH2:2])([CH3:15])[CH3:14])=[CH2... | C=C[Si](C=C)(C=C)C=C | C[SiH](C)O[SiH](C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 70 | null | To the 25 ml round bottomed flask equipped with a reflex condenser was charged 10.17 g of tetravinylsilane (75 mmol), 1 g of 1,1,3,3-tetramethyldisiloxane (7.5 mmol) and 10 μL of platinumdivinylmethyldisiloxane (5% Pt). The mixture was stirred and heated at 70° C. until it turned light yellow. (Scheme 5) . From this mi... | C=C[Si](C=C)(C=C)CC[Si](C)(C)O[Si](C)(C)CC[Si](C=C)(C=C)C=C | null | 28.8 | null |
434,483 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[CH2:28]([NH:30][CH2:31][CH2:32][OH:33])[CH3:29]>>[CH2:28]([N:30]([CH2:31][CH2:32][OH:33])[C:23]([C:22]1[CH:21]=[CH:20][C... | CC(C)Nc1cccnc1N1CCN(C(=O)c2ccc(C(=O)O)cc2)CC1 | CCNCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the same procedure as described in the example 1, synthesis was carried out starting with 4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid and using 2-(ethylamino)ethanol. Then, the product was recrystallized using ethyl acetate and petroleum ether, filtered and dried to give the desired compo... | CCN(CCO)C(=O)c1ccc(C(=O)N2CCN(c3ncccc3NC(C)C)CC2)cc1 | null | 86 | null |
1,767,313 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH:1]1([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][NH:2]1.[C:16]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]([C:22](O)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1>>[C:16]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]([C:22]([N:2]2[CH2:3][CH:4]3[CH:9... | CCOC(=O)CC1NCC2CCCCC21 | O=C(O)c1ccccc1-c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl 2-(2-(biphenylcarbonyl)octahydro-1H-isoindol-1-yl)acetate was prepared according to general procedure A using ethyl 2-(octahydro-1H-isoindol-1-yl)acetate and biphenyl-2-carboxylic acid. | CCOC(=O)CC1C2CCCCC2CN1C(=O)c1ccccc1-c1ccccc1 | null | null | null |
589,582 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[C:12](F)[C:11]([C:15]#[N:16])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].[CH3:21][NH:22][CH3:23]>CS(C)=O>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[C:12]([N:22]([CH3:23])[CH3:21])[C:11]([C:15]#[N:16])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18])([CH3:4])([... | CC(C)(C)OC(=O)Nc1cc(F)c(C#N)cc1[N+](=O)[O-] | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (4-cyano-5-fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester (Example B9) (2.0 g, 7.11 mmol) and dimethylamine (6.3 ml, 33% in EtOH, 35.0 mmol) in DMSO (30 mL) at RT according to the general procedure C. Obtained as a yellow solid (1.87 g, 86%). | CN(C)c1cc(NC(=O)OC(C)(C)C)c([N+](=O)[O-])cc1C#N | null | null | null |
182,166 | ord_dataset-f25e1b7f8ef54305a5170f5395a768c7 | null | 1989-01-01T00:01:00 | true | S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([N+]([O-])=O)=[C:12]([NH:20][C:21]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:22](=[N:25]O)[CH2:23][OH:24])[N:11]=1>[OH-].[Na+]>[NH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]2[N:25]=[C:22]([CH2:23][OH:24])[C:21]([CH2:29][CH3:30])([CH2:27][CH3:28])[NH:20... | CCC(CC)(Nc1nc(N)nc(O)c1[N+](=O)[O-])C(CO)=NO | null | null | O=S([O-])S(=O)[O-] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Sodium dithionite was added portionwise to a warm solution of 2-amino-4-hydroxy-6-(1,1-diethyl-3-hydroxy-2-hydroxyiminopropylamino)-5-nitropyrimidine (450 mg) in 0.1M sodium hydroxide until the colour changed from red to very pale yellow. A solid product was not obtained either on cooling or on adjusting the pH. In ord... | CCC1(CC)Nc2nc(N)nc(O)c2N=C1CO | null | 2.8 | null |
1,352,632 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | N#N.[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16]O)=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].CCN(CC)CC.S([Cl:31])(C)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][Cl:31])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4] | CC(O[Si](C)(C)C(C)(C)C)c1ncc(CO)o1 | CS(=O)(=O)Cl | null | CN(C)c1ccncc1 | N#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 0 | null | In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-yl-methanol (760 mg, 2.95 mmol) in dry CH2Cl2 (15 mL) was treated at 0° C. with Et3N (0.53 mL, 3.82 mmol) followed by DMAP (36 mg, 0.30 mmol) and M... | CC(O[Si](C)(C)C(C)(C)C)c1ncc(CCl)o1 | null | null | null |
1,185,872 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1)=[O:15].N#N.N1C=CC=CC=1.[F:39][C:40]([F:46])([F:45])[S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:13][O:12][C:7... | O=S(=O)(Cl)C(F)(F)F | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(O)ccc2c1 | null | N#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 0.25 | Dissolve (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone in CH2Cl2 (10 volumes) in a three neck round bottom flask equipped with a stir bar and N2 source and chill to 0° C. in an ice/brine bath. Add pyridine (1.3 equivalents). Add trifluoromethane sulfonyl chloride (1.2 equivalents)... | COc1ccc2c(C(=O)c3ccc(OCCN4CCCCC4)cc3)c(OS(=O)(=O)C(F)(F)F)ccc2c1 | null | null | null |
66,508 | ord_dataset-8af141577c90485cb9c91079a5ef96b3 | null | 1980-01-01T00:05:00 | true | [O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:21])[C:18](N)=[O:19])[CH:15]=[CH:16][C:3]1=2.[OH-].[K+].O.C([OH:27])C>C(O)(=O)C>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:21])[C:18]([OH:27])=[O:19])[CH:15]=[CH:16]... | CCO | CC(C(N)=O)c1ccc2c(c1)Sc1ncccc1CC2=O | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | 0 | null | The mixture of 100 mg of 2-(5,6-dihydro-6-oxo benzo[b]-pyrido[3,2-f]thiepin-9-yl)-propionamide, 170 mg of potassium hydroxide, 1.5 ml of water and 3 ml of ethanol was refluxed for 5 hours. After cooling, the solvent was distilled off to obtain the residue, to which was added ice-water and the resulting mixture was acid... | CC(C(=O)O)c1ccc2c(c1)Sc1ncccc1CC2=O | null | null | null |
1,682,141 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [CH:1]1([NH:4][C:5]([C@@H:7]2[C@H:12]([NH:13][C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([NH2:21])[C:15]=3[NH2:22])[C@@H:11]3[CH2:23][C@H:8]2[CH:9]=[CH:10]3)=[O:6])[CH2:3][CH2:2]1.[Cl:24][C:25]1[N:26]=[C:27]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[S:28][C:29]=1[CH:30]=O.C([O-])(=O)C.[NH4+]>>[CH:1]1([NH:4][C:5](... | O=Cc1sc(N2CCOCC2)nc1Cl | Nc1ncc(Cl)c(N[C@H]2[C@@H](C(=O)NC3CC3)[C@@H]3C=C[C@H]2C3)c1N | null | CC(=O)[O-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid cyclopropylamide (200 mg, 0.6 mmol), 4-Chloro-2-morpholin-4-yl-thiazole-5-carbaldehyde (0.17426 g, 0.74892 mmol), and Ammonium acetate (92.439 mg, 1.1992 mmol) were reacted to pr... | O=C(NC1CC1)[C@@H]1[C@H](Nc2c(Cl)cnc3[nH]c(-c4sc(N5CCOCC5)nc4Cl)nc23)[C@H]2C=C[C@@H]1C2 | null | 7.1 | null |
1,219,437 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([NH:23][CH:24]([CH3:26])[CH3:25])[N:17]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[OH:4].[C:27](O)(=[O:30])[CH2:28][OH:29]>>[OH:30][CH2:27][C:28]([NH:1][CH2:2][CH:3]([OH:4])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:... | Cc1cc(-c2nc(-c3ccc(C(O)CN)cc3)no2)nc(NC(C)C)n1 | O=C(O)CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared in analogy to Example 127 using rac-2-amino-1-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol (Example 144) and glycolic acid; LC-MS: tR=0.81 min; [M+H]+=413.03. | Cc1cc(-c2nc(-c3ccc(C(O)CNC(=O)CO)cc3)no2)nc(NC(C)C)n1 | null | null | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.