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 ⌀ |
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1,445,407 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH:11]1([C:14]2[C:22]3[C:17](=[CH:18][C:19]([CH:23]=O)=[CH:20][CH:21]=3)[N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[N:15]=2)[CH2:13][CH2:12]1>>[CH:11]1([C:14]2[C:22]3[C:17](=[CH:18][C:19](/[CH:23]=[C:3]4/[C:2](=[O:10])[N... | C[Si](C)(C)CCOCn1nc(C2CC2)c2ccc(C=O)cc21 | O=C1Cc2ccccc2N1 | 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 | According to the method of Example A19, indolin-2-one (17 mg, 0.13 mmol) and 3-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (40 mg, 0.13 mmol) were reacted to obtain crude product. The crude mixture was purified by prepTLC (SiO2 2% MeOH in DCM) to provide the title compound as a yellow so... | C[Si](C)(C)CCOCn1nc(C2CC2)c2ccc(/C=C3/C(=O)Nc4ccccc43)cc21 | null | 85.5 | null |
766,441 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][O:12][N:13]2C(=O)C3=CC=CC=C3C2=O)=[CH:3][CH:2]=1.NN>CCO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][O:12][NH2:13])=[CH:3][CH:2]=1 | O=C1c2ccccc2C(=O)N1OCc1ccnc2ccccc12 | null | null | NN | 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 | 3 | N-(4-quinolyl)methoxy phthalimide (2.00 g) was suspended in 95% EtOH and hydrazine (0.30 mL) was added. The reaction mixture was stirred for 3 h and then filtered. The filtrate was concentrated under reduced pressure and then taken up in a small amount of dichloromethane. The small amount of remaining phthalhydrazide w... | NOCc1ccnc2ccccc12 | null | 125.8 | null |
1,694,136 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Br:1][C:2]1[C:11]2[C:6](=[C:7]([Br:21])[CH:8]=[C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:22][CH3:23])[CH:3]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1>O1CCCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[... | Clc1ccc([Mg]Br)cc1 | COc1cc(Br)c2cc(C(=O)c3ccc(Cl)cc3)cc(Br)c2n1 | 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 | 25 | 3 | Into a 100-mL round-bottom flask, was placed a solution of 4,8-dibromo-6-[(4-chlorophenyl)carbonyl]-2-methoxyquinoline (1.5 g, 3.29 mmol, 1.00 equip) in tetrahydrofuran (30 mL). To the resulting mixture was then added (4-chlorophenyl)magnesium bromide (9.87 mL, 3.00 equip, 1 M) dropwise with stirring at 0° C. The resul... | COc1cc(Br)c2cc(C(O)(c3ccc(Cl)cc3)c3ccc(Cl)cc3)cc(Br)c2n1 | null | null | null |
163,575 | ord_dataset-f5dc3e448c204058b116bf1970695bef | null | 1987-01-01T00:09:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=O)[CH2:7]Cl)#[N:2].[C:13]([NH:16][C:17]([NH2:19])=[S:18])(=[NH:15])[NH2:14]>CCO>[NH:16]([C:17]1[S:18][CH:7]=[C:6]([C:5]2[CH:4]=[C:3]([CH:12]=[CH:11][CH:10]=2)[C:1]#[N:2])[N:19]=1)[C:13]([NH2:15])=[NH:14] | N=C(N)NC(N)=S | N#Cc1cccc(C(=O)CCl)c1 | null | null | 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 | A mixture of 3-cyanophenacyl chloride (1.78 g.) and amidinothiourea (1.2 g.) in EtOH (40 ml.) was heated under reflux for 1 hour. The solid precipitate was filtered off, dissolved in hot water (100 ml.) and the solution basified with sodium bicarbonate. The precipitated solid was filtered off and dried to give 3-[2-gua... | N#Cc1cccc(-c2csc(NC(=N)N)n2)c1 | null | null | null |
1,260,938 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | Cl[CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[NH:8]1[CH2:13][CH2:12][C:11](=[C:14]2[C:23]3[CH:24]=[C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:27][C:22]=3[O:21][CH2:20][C:19]3[CH:18]=[CH:17][S:16][C:15]2=3)[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[O:7]=[C:5]([CH3:6])[CH2:4][CH2:3][CH2:2]... | CC(=O)CCCCl | COC(=O)Cc1ccc2c(c1)C(=C1CCNCC1)c1sccc1CO2 | null | O=C([O-])[O-] | [I-] | [K+] | 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 | 8 | 5-Chloro-2-pentanone (2.4 mL, 20.9 mmol) was added to a DMF (50 mL) solution of methyl (4-piperidin-4-ylidene-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl)acetate (2.50 g, 7.0 mmol), anhydrous potassium carbonate (2.15 g, 15.6 mmol), and potassium iodide (1.41 g, 8.5 mmol), and the mixture was stirred overnight at 80° ... | COC(=O)Cc1ccc2c(c1)C(=C1CCN(CCCC(C)=O)CC1)c1sccc1CO2 | null | 78 | null |
934,246 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([CH3:24])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([CH3:24])[N:16]=2)[CH2:12][CH2:13]1)=... | Cc1nc(OC2CCN(C(=O)OC(C)(C)C)CC2)ccc1[N+](=O)[O-] | 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 | null | Stir a mixture of 4-(6-methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (2.69 g, 8.0 mmol) and 10% palladium on carbon (1.0 g) in ethanol (60 mL) at 22° C. under hydrogen for 2 hours. Filter off the palladium catalyst. Concentrate the filtrate to give a colorless oil. Subject residue to sil... | Cc1nc(OC2CCN(C(=O)OC(C)(C)C)CC2)ccc1N | null | 89 | null |
509,074 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([NH:20][C:21]#[N:22])=[N:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[N:15]3)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.N1C=CC=CC=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](... | N#CNC(=Nc1cccc2ncccc12)NCc1ccc(N)cc1 | O=S(=O)(Cl)c1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 12 | N-(4-Amino-benzyl)-N′-cyano-N″-quinolin-5-yl-guanidine (50 mg, 0.16 mmol) and 4-chloro-benzenesulfonyl chloride (41 mg, 0.19 mmol) were added to pyridine (1 mL). An exothermic reaction occurred and the suspension became homogeneous. This solution was shaken at room temperature for 12 hours. The reaction mixture was the... | N#CN=C(NCc1ccc(NS(=O)(=O)c2ccc(Cl)cc2)cc1)Nc1cccc2ncccc12 | null | 76 | null |
636,886 | ord_dataset-a192df1b44174b5886ef2005f759d553 | null | 2004-01-01T00:05:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[C:2]1=[N:11][OH:12].C[O-].[Na+].Br[CH2:17][CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1.O>CO>[O:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]1[O:19][CH2:18][CH2:17][O:12][N:11]=[C:2]1[C:3](=[O:10])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1 | O=C1C(=NO)Oc2ccccc21 | BrCCOC1CCCCO1 | null | C[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 | 20 | 16 | 5 g (0.03 mol) of benzofuran-2,3-dione 2-oxime (XI-1) are dissolved in 30 ml of methanol, and at 20° C. 15 ml of a 2 molar solution of sodium methoxide in methanol are added dropwise. The solvent is distilled off under reduced pressure. The crystalline residue is dissolved in 30 ml of N-methyl-2-pyrrolidinone and treat... | O=C1C(=NOCCOC2CCCCO2)Oc2ccccc21 | null | 63.5 | null |
600,575 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12]1[C:13](=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:14](O)=O.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:14]1[C:13]2[C:12]([N:11]=[C:3]3[C:4]=1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:2]3[CH3:1])=[CH:20][CH:19]=[C:18]([O:21][CH3:22])[CH:17]... | O=P(Cl)(Cl)Cl | COc1ccc(Nc2cc([N+](=O)[O-])ccc2C)c(C(=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 | N-(2′-methyl-5′-nitrophenyl)-5-methoxyanthranilic acid (7.2 g) is heated in phosphorous oxychloride (60 ml) at 120° C. for 1 hour. Excess phosphorous oxychloride is distilled off under reduced pressure, and the residue poured slowly into a stirred mixture of chloroform, concentrated ammonium hydroxide and ice. The sepa... | COc1ccc2nc3c(C)ccc([N+](=O)[O-])c3c(Cl)c2c1 | null | 68 | null |
1,627,120 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [Br:1][C:2]1[CH:8]=[C:7]([O:9]C)[C:5]([NH2:6])=[CH:4][C:3]=1[Cl:11].B(Br)(Br)Br>C(Cl)Cl>[NH2:6][C:5]1[CH:4]=[C:3]([Cl:11])[C:2]([Br:1])=[CH:8][C:7]=1[OH:9] | COc1cc(Br)c(Cl)cc1N | null | null | BrB(Br)Br | 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 | 2 | To a suspension of 4-bromo-3-chloro-6-methoxyaniline (28) (944 mg, 4 mmol) in 10 ml DCM was added 1 M BBr3 in DCM (8 ml, 8 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extrac... | Nc1cc(Cl)c(Br)cc1O | null | 97.2 | null |
1,409,303 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[Na+].[Na+]>CO.S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([O:6][CH3:12])=[O:5] | O=C([O-])[O-] | O=C(O)c1c(F)cccc1Br | null | O=S(=O)(O)O | [Na+] | 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 | 80 | 12 | 2-Bromo-6-fluorobenzoic acid (1, 12.50 g, 57 mmol) was dissolved in a mixture of methanol (60 mL) and conc. sulfuric acid (65 mL). The solution was heated to 80° C. and stirred for 12 h. The reaction mixture was cooled and 20% sodium carbonate solution (500 mL) was added slowly to reach pH=8. The mixture was extracted ... | COC(=O)c1c(F)cccc1Br | null | 85 | null |
1,555,738 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Br:1][C:2]1[N:6]2[N:7]=[C:8](F)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.O.[NH2:13][NH2:14]>>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:13][NH2:14])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1 | NN | Fc1ccc2ncc(Br)n2n1 | null | null | null | null | 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 | 70 | null | A suspension of 3-bromo-6-fluoroimidazo[1,2-b]pyridazine (2.16 g, 10 mmol) in hydrazine monohydrate (10 mL) was heated at 70° C. for 30 minutes. The mixture was cooled to room temperature, and the titled compound (1.78 g) was collected by filtration. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.27 (br. s., 2H) 6.78 (d, J=9.60 Hz,... | NNc1ccc2ncc(Br)n2n1 | null | null | null |
584,988 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | C1C2C(COC([N:18]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@H:19]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([OH:37])[CH:31]=3)=[O:27])[CH2:20][CH2:21][C:22](=[O:25])[NH:23][CH3:24])=O)C3... | CNC(=O)CC[C@@H](C(=O)NCc1ccc(O)c(O)c1)N(C(=O)OCC1c2ccccc2-c2ccccc21)C(c1ccccc1)(c1ccccc1)c1ccccc1 | O=C(O)c1cc(O)c2cccc(O)c2n1 | 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 N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamine (1.0 g, 1.4 mmol, example 26, step A) as described for example 26 using 4,8-dihydroxyquinoline-2-carboxylic acid (435 mg, 2.1 mmol) instead of4-hydroxy-3-nitrobenzoic acid. The crude material w... | CNC(=O)CC[C@@H](C(=O)NCc1ccc(O)c(O)c1)N(C(=O)c1cc(O)c2cccc(O)c2n1)C(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null |
203,362 | ord_dataset-76a008eb2d3f48d891cad325041f3d1e | null | 1990-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH:10]([NH:12][C:13](=[O:17])OCC)[CH3:11])[CH:5]=[CH:6][C:7]=1[OH:8].O.[NH2:20][NH2:21].O>C(O)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]([CH3:11])[NH:12][C:13](=[O:17])[NH:20][N:21]=2)[CH:5]=[CH:6][C:7]=1[OH:8] | NN | CCOC(=O)NC(C)C(=O)c1ccc(O)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCCCO | null | null | null | null | null | null | null | null | null | null | null | 32.64 g of ethyl N-[2-(3-chloro-4-hydroxyphenyl)-1-methyl-2-oxoethyl]carbamate [prepared as described in Example 1(b)] and 75.20 g of 80% hydrazine hydrate (i.e. a grade of hydrazine hydrate containing 20% w/w water) were added to 240 ml of butanol, and the mixture was heated under reflux for 18 hours. The butanol used... | CC1NC(=O)NN=C1c1ccc(O)c(Cl)c1 | null | 51.1 | null |
956,489 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH2:1](C1NC(C(OCC)=O)=CC=1)C.[Cl:13][C:14]1[C:18]([Cl:19])=[C:17]([CH3:20])[NH:16][C:15]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[Cl:13][C:14]1[C:18]([Cl:19])=[C:17]([CH2:20][CH3:1])[NH:16][C:15]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22] | CCOC(=O)c1[nH]c(C)c(Cl)c1Cl | CCOC(=O)c1ccc(CC)[nH]1 | 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 | Title compound was synthesized from ethyl 5-ethyl-1H-pyrrole-2-carboxylate (Intermediate 12) by an analogous method to Intermediate 4. | CCOC(=O)c1[nH]c(CC)c(Cl)c1Cl | null | null | null |
155,276 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[SH:10][CH2:11][C:12](O)=[O:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[SH:10][CH2:11][C:12]([O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:13] | O=C(O)CS | OC1CCCCCCC1 | null | Cc1ccc(S(=O)(=O)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 | Into a 100 ml reaction flask equipped with stirrer, thermometer, reflux condenser and heating mantle are placed 32 grams of cyclooctanol; 9.2 grams of mercaptoacetic acid and 0.5 grams paratoluene sulfonic acid. | O=C(CS)OC1CCCCCCC1 | null | null | null |
1,584,005 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH3:1][CH:2]1[NH:6][CH2:5][C:4]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[S:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][CH2:38][C:39](O)=[O:40])=[CH:29]1>ClCCl>[CH3:1][CH:2]1[N:6]([C:39](=[O:40])[CH2:38][CH2:37][C:30]2[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][C... | CC1NCC2(CCN(C)CC2)S1 | O=C(O)CCc1c[nH]c2ccccc12 | null | C(=NC1CCCCC1)=NC1CCCCC1 | 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 | 8 | To a stirred solution of 2,8-dimethyl-1-thia-3,8-diaza-spiro[4.5]decane (2.18 g, 11.7 mmol) in dichloromethane (230 ml) at room temperature was added dicyclohexylcarbodiimide (DCC) (3.24 g, 15.7 mmol) followed by addition of 3-indolepropionic acid (2.87 g, 15.2 mmol). The resulting solution was stirred at room temperat... | CC1SC2(CCN(C)CC2)CN1C(=O)CCc1c[nH]c2ccccc12 | null | null | null |
924,072 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [H-].[Na+].[Br:3][C:4]1[C:5]([C:9]#[N:10])=[N:6][NH:7][CH:8]=1.[CH3:11]I>CN(C=O)C>[Br:3][C:4]1[C:5]([C:9]#[N:10])=[N:6][N:7]([CH3:11])[CH:8]=1 | CI | N#Cc1n[nH]cc1Br | 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 | 0 | 1 | Add sodium hydride (60 wt % oil dispersion, 700 mg, 17.5 mmol) in several portions under a nitrogen purge to a solution of 4-bromo-1H-pyrazole-3-carbonitrile (2.0 g, 11.6 mmol) in 15 mL of anhydrous DMF at 0° C. Stir the reaction at 0° C. for one hour. Add methyl iodide (0.9 mL, 14.5 mmol) to the mixture and allow to s... | Cn1cc(Br)c(C#N)n1 | null | 64 | null |
1,582,129 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Br.Br[CH:12]([C:14]1[CH:15]=[C:16]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])[CH:17]=[C:18]2[C:23]=1[O:22][C:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[CH:20][C:19]2=[O:30])[CH3:13]>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][CH:12]([C:14]2[CH:15]=[C:16]([C:31]([N:3... | Nc1ccc(F)c(F)c1 | CC(Br)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | null | Br | 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 | 3,4-difluoroaniline (0.105 mL, 1.06 mmol) was reacted with 8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (130 mg, 0.27 mmol) using a procedure similar to the one described in Example 3.00 to give 8-(1-(3,4-difluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6... | CC(Nc1ccc(F)c(F)c1)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | null | 28.3 | null |
1,274,864 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C[O:2][C:3]([C:5]1[S:6][C:7]([C:11](=[O:21])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)=[CH:8][C:9]=1[Br:10])=[O:4].O.[OH-].[Li+].C1COCC1.Cl>O>[Br:10][C:9]1[CH:8]=[C:7]([C:11](=[O:21])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2] | COC(=O)c1sc(C(=O)NCc2cccc(O)c2)cc1Br | null | null | Cl | [Li+] | [OH-] | 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 | 15 | A mixture of 3-Bromo-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carboxylic acid methyl ester (160 mg, 0.43 mmol), lithium hydroxide monohydrate (180, mg, 4.32 mmol), THF (5 mL) and water (6 mL) was stirred 15 h, acidified with 1N HCl and extracted with EtOAc (×3). The organic extracts were combined, washed with brine, d... | O=C(NCc1cccc(O)c1)c1cc(Br)c(C(=O)O)s1 | null | null | null |
309,342 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[Br:17]Br>C(Cl)(Cl)(Cl)Cl>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH2:1][Br:17])=[CH:7][CH:6]=1)([O-:16])=[O:15] | BrBr | Cc1ccc(-c2ccccc2[N+](=O)[O-])cc1 | null | null | 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 | 25 | null | 4-Methyl-2'-nitrobiphenyl (from Step A) (2.173 g, 10.2 mmol) was dissolved in CCl4 (100 mL) and heated to reflux with stirring. To this was added a bromine solution [prepared by diluting 11.2 ml (11.2 mmole) of commercial 1.0M solution in CCl14 to a final volume of 40 mL with CCl4 ] dropwise while a 100 W lamp was used... | O=[N+]([O-])c1ccccc1-c1ccc(CBr)cc1 | null | 90 | null |
147,628 | ord_dataset-2069a3db775a4d9f9310aca092ecbad8 | null | 1986-01-01T00:08:00 | true | [CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[C:6]([CH2:9][N:10]1[C:14](=[O:15])[C:13](=[CH:16]OCC)[S:12][C:11]1=[S:20])([OH:8])=[O:7]>C(O)C>[C:6]([CH2:9][N:10]1[C:14](=[O:15])[C:13](=[CH:16][NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])[S:12][C:11]1=[S:20])([OH:8])=[O:7] | CC(C)CN | CCOC=C1SC(=S)N(CC(=O)O)C1=O | null | null | 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 | 0.74 Gram (0.01 mole) of isobutylamine was added to a mixture of 1.2 g (0.005 mole) of 3-carboxymethyl-5-ethoxymethylidenerhodanine and 10 ml of ethanol, and the resulting mixture was subjected to reaction at a temperature of 50° to 60° C. for 1 hour. The reaction mixture was concentrated and the resulting residue was ... | CC(C)CNC=C1SC(=S)N(CC(=O)O)C1=O | null | 65.6 | null |
1,540,875 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][C:2]([F:9])([F:8])[C:3](=O)[CH2:4][C:5]#[N:6].[Cl:10][C:11]1[C:12]([O:19][CH3:20])=[C:13]([NH:17][NH2:18])[CH:14]=[CH:15][CH:16]=1>C(O)C>[Cl:10][C:11]1[C:12]([O:19][CH3:20])=[C:13]([N:17]2[C:5]([NH2:6])=[CH:4][C:3]([C:2]([F:9])([F:8])[F:1])=[N:18]2)[CH:14]=[CH:15][CH:16]=1 | N#CCC(=O)C(F)(F)F | COc1c(Cl)cccc1NN | null | null | 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 | To a stirred solution of 4,4,4-trifluoro-3-oxobutanenitrile (1.64 g, 11.96 mmol, 1.0 eq) in ethanol (15 mL) was added (3-chloro-2-methoxyphenyl)hydrazine (2.5 g, 11.96 mmol, 1.0 eq) and the mixture was refluxed for 3 h. Ethanol was evaporated, the mixture diluted with water and extracted with ethyl acetate (300 mL×2), ... | COc1c(Cl)cccc1-n1nc(C(F)(F)F)cc1N | null | 24.1 | null |
240,674 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | [C:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17](=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:12]([F:25])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(OC(=O)C)(=O)C.C(OCC)(OCC)OCC>[C:1]([N:4]1[CH2:5][CH:6]=[C:7]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17](=[O:24])[C:18](=[CH:22][O:21... | CCOC(=O)CC(=O)c1cc(F)c(C2=CCN(C(C)=O)CC2)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(OCC)OCC | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A solution of 3.95 g (11.25 mmol) ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-4-pyridyl)-2,5-difluoro-β-oxobenzenepropionate in 25 ml of acetic anhydride and 2.8 ml of trietyl orthoformate was refluxed 1.5 hours. The title compound was isolated as a syrup after evaporation under vacuum in an oil bath at 80° C. | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(C2=CCN(C(C)=O)CC2)cc1F | null | null | null |
908,674 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:15]=2[CH3:22])=[C:12]2[C:7]([C:8]([C:23]([F:26])([F:25])[F:24])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:1][C:2]1[CH:30]=[C:29]([CH3:31])[CH:28]=[... | COc1ccc(-c2c3cccc(C(F)(F)F)c3nn2Cc2ccc(C)cc2C)c(C)c1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | ClB(Cl)Cl | [I-] | 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 | null | A solution of 2-(2,4-Dimethylbenzyl)-3-(4-methoxy-2-methylphenyl)-7-trifluoromethyl-2H-indazole (0.27 g, 0.63 mmol) and tetrabutylammonium iodide (0.7 g, 1.9 mmol) in 10 mL of CH2Cl2 was cooled to −78° C. and treated with boron trichloride 1M in CH2Cl2 (1.9 mL, 1.9 mmol). The reaction mixture was allowed to warm to amb... | Cc1ccc(Cn2nc3c(C(F)(F)F)cccc3c2-c2ccc(O)cc2C)c(C)c1 | null | 69.6 | null |
1,568,603 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][N:13]([CH3:15])[NH2:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:12][N:13]([CH3:15])[NH:14][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=1 | Nc1cc(Cl)ccc1[N+](=O)[O-] | CN(C)N | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | 125 | 72 | A mixture of 5-chloro-2-nitroaniline (20 g, 116 mmol), N,N-dimethyl-hydrazine (44 mL, 580 mmol) and anhydrous potassium carbonate (17.6 g, 128 mmol) in N,N-dimethylacetamide (50 ml) were stirred at 125° C. under nitrogen for 3 days Sample NMR analysis showed complete conversion of the starting material. The resultant m... | CN(C)Nc1ccc([N+](=O)[O-])c(N)c1 | null | 47 | null |
185,216 | ord_dataset-754e10d30fb249229e130865010ab25b | null | 1989-01-01T00:03:00 | true | [C:1]([N:4]1[CH2:9][CH2:8][C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2N)([C:10]#[CH:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.N([O-])=O.[Na+]>O>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([C:10](=[CH2:11])[C:14]3[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=3[O:12]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2] | C#CC1(Oc2ccc(F)cc2N)CCN(C(C)=O)CC1 | null | null | Cl | O=N[O-] | [Na+] | 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 | null | 0.46 | A stirred suspension of 19.4 g of 1-N-acetyl-4-(2-amino-4-fluorophenoxy)-4-ethynylpiperidine, 91 ml of water and 6.9 ml of hydrochloric acid was heated at reflux until the starting material dissolved. The mixture was then cooled to below 10°. To the mixture was added slowly, dropwise, 7.6 ml of concentrated hydrochlori... | C=C1c2cc(F)ccc2OC12CCN(C(C)=O)CC2 | null | 25.7 | null |
286,385 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [C:1]([Cl:4])(Cl)=[O:2].O[C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CC1C=CC=CC=1C>[Cl:4][C:1]([C:15]1[CH:16]=[CH:17][C:12]([C:10]([C:9]2[CH:18]=[CH:19][CH:6]=[CH:7][CH:8]=2)=[O:11])=[CH:13][CH:14]=1)=[O:2] | O=C(Cl)Cl | O=C(c1ccccc1)c1ccc(O)cc1 | null | C[N+](C)(C)Cc1ccccc1 | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | 0.5 | A total of 3.4 kg of phosgene was passed through a solution of 4 kg of 4-hydroxybenzophenone and 190 g of benzyltrimethylammonium chloride in 11.4 kg of o-xylene over a period of 5 hours, during which time the internal temperature was raised from 95° to 120° C. The introduction of phosgene was then stopped, and stirrin... | O=C(Cl)c1ccc(C(=O)c2ccccc2)cc1 | null | 99.2 | null |
974,299 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | C([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14]1)[CH2:8][CH2:7]2)(O)=O.[N-:20]=[N+]=[N-].[Na+].[OH-].[Na+]>OS(O)(=O)=O>[NH2:20][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14]1)[CH2:8][CH2:7]2 | O=C1NC(=O)C2(CCc3cc(C(=O)O)ccc3C2)N1 | [N-]=[N+]=[N-] | null | O=S(=O)(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 | 50 | null | A stirred mixture of (±)-6′-carboxy-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (described in Intermediate 1) (1.50 g, 5.76 mmol), and sodium azide (749 mg, 11.53 mmol) in conc. H2SO4 (30 mL) was heated to 50° C. for 2 h, then allowed to cool to ambient temperature. The mixture was adjusted to pH ... | Nc1ccc2c(c1)CCC1(C2)NC(=O)NC1=O | null | null | null |
1,253,630 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]([O:23]C)=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]([OH:23])=[O:22])[CH2:10]... | COC(=O)c1cc(F)ccc1N1CCN(C(=O)OC(C)(C)C)CC1 | null | null | [Li+] | [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 | 50 | null | 4-(4-Fluoro-2-methoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (5.5 g, 16.2 mmol) is dissolved in THF (40 mL) and 1 M aqueous LiOH (33 mL) is added at room temperature. The solution is warmed to 50° C. for 3 h. THF is removed under reduced pressure and the aqueous part is washed with 50% EtOAc in h... | CC(C)(C)OC(=O)N1CCN(c2ccc(F)cc2C(=O)O)CC1 | null | 93.3 | null |
210,161 | ord_dataset-e0a818f9350b46cdb184d2ac404ede9f | null | 1990-01-01T00:06:00 | true | Cl[CH2:2][CH:3]([OH:16])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+]>O>[CH2:6]([O:5][CH2:4][CH:3]1[CH2:2][O:16]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15] | CCCCCCCCCCOCC(O)CCl | null | null | [Na+] | [OH-] | null | 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 | 40 | null | To the crude 1-chloro-3-decyloxy-2-propanol prepared as described above and cooled to 40° C. was added NaOH (50% aqueous, 176 g, 2.2 mole) and water (44 g). The temperature rose to 50° C., then the mixture was heated to 85° C.-90° C. for three hours. Analysis by GC showed the crude product contained 11% unreacted alcoh... | CCCCCCCCCCOCC1CO1 | null | 67 | null |
399,759 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [CH2:1]([O:3][P:4]([CH:9]1[N:14]2[C:15](=[O:27])[C:16](=[O:26])[NH:17][C:18]3[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=[C:12]([C:13]=32)[CH2:11][CH2:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].F[B-](F)(F)F.[O:33]=[N+:34]=[O:35]>ClCCl>[CH2:6]([O:5][P:4]([CH:9]1[N:14]2[C:15](=[O:27])[C:16](=[O:26])[NH:17][C:18]3[C... | O=[N+]=O | CCOP(=O)(OCC)C1CCc2cc(C(F)(F)F)cc3[nH]c(=O)c(=O)n1c23 | null | F[B-](F)(F)F | 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 | null | 15 | 812 mg of 9-trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid diethyl ester is dissolved in 15 ml of dichloromethane and mixed with 531 mg of nitronium tetrafluoroborate at room temperature. It is stirred for 15 hours and concentrated by evaporation. The residue is taken up i... | CCOP(=O)(OCC)C1CCc2c([N+](=O)[O-])c(C(F)(F)F)cc3[nH]c(=O)c(=O)n1c23 | null | 52.1 | null |
428,710 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | C([Li])CCC.[CH3:6][C:7]1[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([CH2:6][C:7]2[C:8]... | COc1cc(OC)nc(S(C)(=O)=O)n1 | Cc1cccnc1NC(=O)OC(C)(C)C | null | [Cl-] | [Li]CCCC | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | -70 | 0.33 | n-Butyllithium (19.2 ml of a 2.5M solution in hexane) was added dropwise to a stirred suspension of the product of stage (a) above (5.0 g) in dry tetrahydrofuran (100 ml) under nitrogen at -70° C. The mixture was stirred at -70° C. for 20 minutes and then at 5° C. for 3 hours. It was then cooled to -70° C. and treated ... | COc1cc(OC)nc(Cc2cccnc2NC(=O)OC(C)(C)C)n1 | null | null | null |
1,405,048 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][C:22]1N(C)N=NN=1.ClC1[C:38](=[O:39])C2C(=CC=CC=2)C(=O)C=1NC1C=CC(S(NC2C=C(C)C=CC=2)(=O)=O)=C(OC)C=1>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12]... | Cn1nnnc1Sc1cc(NS(=O)(=O)c2cccs2)c2ccccc2c1O | COc1cc(NC2=C(Cl)C(=O)c3ccccc3C2=O)ccc1S(=O)(=O)Nc1cccc(C)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 | 5.2.53 N-(4-hydroxy-3-(2-hydroxyethylthio)naphthalen-1-yl)thiophene-2-sulfonamide (14k) was prepared according to the procedure for 14d except using N-(3-(2-hydroxyethylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (13k), which, after purification via flash chromatography (Hex/EtOAc), afforded the title c... | O=S(=O)(Nc1cc(SCCO)c(O)c2ccccc12)c1cccs1 | null | null | null |
691,622 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[N:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[F:23][C:24]1[C:29]([C:30]#[N:31])=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([C:2]2[CH:3]=[C:4]([C:9]3[N:10]=[C:11]([... | Fc1ccc(-c2nncc(-c3ccc(F)c(Br)c3)n2)c(F)c1 | CC1(C)OB(c2cccc(F)c2C#N)OC1(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 | null | null | 5-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine was coupled to 6-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile by the method of Example 12 to give 3,2′-difluoro-5′-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]biphenyl-2-carbonitrile as a yellow solid: δH (400 MHz, CDCl3) 6.99-7.1... | N#Cc1c(F)cccc1-c1cc(-c2cnnc(-c3ccc(F)cc3F)n2)ccc1F | null | null | null |
561,107 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]([NH2:20])=O)[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22](N)([CH3:25])[CH2:23][NH2:24].C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:9])[C:18]3=[N:20][C:22]([CH3:25])([CH3:21])[CH2:23][N:24]3[C:10](=[O:17])[C:... | CC(C)(N)CN | NC(=O)C1(c2ccc(Cl)cc2)OC(=O)c2ncccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 3-(4-chlorobenzoyl)-2-pyridinecarboxylic acid (13 g), potassium cyanide (4.56 g), and acetic acid (30 mL) was heated at 120-125 C. in a sealed pressure bottle for 48 h. After cooling to ambient temperature, the mixture was poured into ice water. The precipitated solid was dissolved in ethyl acetate, washed... | CC1(C)CN2C(=O)c3ncccc3C(O)(c3ccc(Cl)cc3)C2=N1 | null | 40.5 | null |
1,181,921 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1)=[O:10].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>>[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4... | Cc1cccc(C(=O)c2cc(Cl)ccc2N)n1 | CC(C)(C)c1ccc(S(=O)(=O)Cl)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 according to the general procedure for the synthesis of N-Aryl-benzenesulfonamides previously described using (2-Amino-5-chloro-phenyl)-(6-methyl-pyridin-2-yl)-methanone and 4-tert-Butyl-benzenesulfonyl chloride and purified by HPLC. 1H NMR: δ 1.29 (s, 9H), 2.94 (s, 3 H), 7.42-7.46 (m, 3... | Cc1cccc(C(=O)c2cc(Cl)ccc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)n1 | null | null | null |
291,956 | ord_dataset-6c3ec086c8c9475e8d31a44641b49e02 | null | 1994-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.C1(P(=[CH:34][C:35]([O:37][CH3:38])=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:34]/[C:35]([O:37][CH3:38])=[O:36])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12] | COc1cc(C=O)cc(OC)c1OC | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | 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 | 25 | 18 | Added to a solution of 8.68 g (0.044 mol) of 3,4,5-trimethoxybenzaldehyde in 50 ml of methanol were 15.0 g (0.044 mol) of methyl (triphenylphosphoranylidene)acetate, followed by stirring at room temperature for 18 hours. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by col... | COC(=O)/C=C/c1cc(OC)c(OC)c(OC)c1 | null | 101.3 | null |
1,247,424 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C(OC([C:6]1[O:7][C:8]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:9]=2[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)C.[Cl-].[Na+].O>CS(C)=O>[CH2:14]([O:13][C:11]([C:10]1[C:9]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:8]=2[O:7][CH:6]=1)=[O:12])[CH3:15] | CCOC(=O)c1oc2cc(OC)ccc2c1C(=O)OCC | null | null | [Cl-] | [Na+] | 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 | 170 | 2 | 6-Methoxy-benzofuran-2,3-dicarboxylic acid diethyl ester (24) (27 g, 92 mmol) is dissolved in 200 ml of a DMSO and the mixture is heated to 170° C. Then sodium chloride (10.7 g, 184 mmol) and water (3.3 ml) are added and the mixture is stirred for 2 h at 160° C. (temperature of reaction mixture). Then the mixture is al... | CCOC(=O)c1coc2cc(OC)ccc12 | null | null | null |
176,146 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | [F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1)=[O:4].[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[F:1][C:2]([F:22])([C:15]([F:20])([F:21])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH... | [N-]=[N+]=[N-] | N#CCc1ccc(NC(=O)C(F)(F)C(F)(F)C(F)(F)F)cc1 | null | [Cl-] | [NH4+] | [Na+] | 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 | null | A mixture of 2,2,3,3,4,4,4-heptafluoro-N-[4-(cyanomethyl)phenyl]butanamide (17.5 g.), sodium azide (17.3 g.) and ammonium chloride (14.1 g.) was heated in dimethylformamide (250 ml.) at 130°-135° C. (oil bath) under a nitrogen atmosphere for 20 hours. Enough water was then added to the hot reaction mixture to dissolve ... | O=C(Nc1ccc(Cc2nnn[nH]2)cc1)C(F)(F)C(F)(F)C(F)(F)F | null | null | null |
1,013,990 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [C:1]([O:6][CH3:7])(=[O:5])[CH:2]([CH3:4])[CH3:3].C([N-]C(C)C)(C)C.[Li+].[CH3:16][Bi:17](Br)[CH3:18]>C1COCC1>[CH3:16][Bi:17]([CH3:18])[C:2]([CH3:4])([CH3:3])[C:1]([O:6][CH3:7])=[O:5] | C[Bi](C)Br | COC(=O)C(C)C | null | CC(C)[N-]C(C)C | [Li+] | 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 | -78 | null | A 2.86 g quantity (28 mmole) of methyl isobutyrate was dissolved in 25 ml of THF, and the mixture was chilled to −78° C. under argon atmosphere. To the mixture was slowly added dropwise 14.0 ml (28 mmole) of lithium diisopropylamide (Aldrich Corp., 2.0M heptane.THF.ethylbenzene solution) over a period of 10 minutes. Th... | COC(=O)C(C)(C)[Bi](C)C | null | 46.9 | null |
1,175,837 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:16][C:17]([O:19][Na])=[O:18]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][CH2:16][C:17]([OH:19])=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | CC(C)(C)OC(=O)N1CC(O)C1 | O=C(CI)O[Na] | 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 | 0.25 | Anhydrous DMF (5 mL) was added slowly to a stirred mixture of 3-hydroxyazetidine-1-carboxylic acid tert-butyl ester (350 mg, 2.0 mmol) and NaH (121 mg of a 60% dispersion in mineral oil, 3.0 mmol) at 0° C. After 15 min, ICH2CO2Na (630 mg, 3.0 mmol) was added, then stirring was continued at 20° C. for 65 h. The solvent ... | CC(C)(C)OC(=O)N1CC(OCC(=O)O)C1 | null | null | null |
868,224 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [NH2:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:15][C:16](N)=[O:17].C1(O)C=CC=CC=1>>[NH:1]1[C:2]2[C:3](=[CH:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH:11]=2)[C:12](=[O:14])[NH:15][C:16]1=[O:17] | Nc1cc2ccccc2cc1C(=O)O | NC(N)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Oc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 185 | null | A mixture of 3-amino-2-naphthoic acid (8-1,1.2 g, 6.6 mmol, 1 equiv), urea (2.0 g, 33 mmol, 5.0 equiv) and phenol (7.0 g, 74 mmol, 11 equiv) was heated at 160° C. for 0.5 h an 185° C. for an additional 1.5 h. The reaction was cooled and triturated with methanol (50 mL). The solid precipitate was filtered, washed with m... | O=c1[nH]c(=O)c2cc3ccccc3cc2[nH]1 | null | null | null |
340,826 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[C:11]([O-])([O-])=O.[Cs+].[Cs+].CI>CC(C)=O>[OH:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH3:11] | O=C([O-])[O-] | OCCc1ccccc1O | null | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CI | null | null | null | null | null | null | null | null | null | 25 | 0.83 | To a solution of 10 g of 2-(2-hydroxyphenyl)-ethanol in 200 ml of acetone there are added 35.3 g of Cs2CO3 and then a solution of 6.5 ml of methyl iodide in 40 ml of acetone. The reaction mixture is stirred for 50 minutes at room temperature, is filtered and is concentrated by evaporation. The residue is partitioned be... | COc1ccccc1CCO | null | null | null |
1,720,710 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)=[C:4]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)(=[O:22])=[O:21])[CH:3]=1.[N:34]1([CH2:39][CH2:40][NH2:41])[CH2:38][CH2:37][CH2:36][CH2:35]1.C(Cl)CCl>CN(C1C... | O=C(O)c1ccc(CSc2ccc(Cl)cc2NS(=O)(=O)c2ccc(Cl)c(C(F)(F)F)c2)cc1 | NCCN1CCCC1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | Following General Procedure R, the title compound (345 mg, 71%) was prepared from 4-({[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}methyl)benzoic acid (410 mg, 0.765 mmol), 2-(pyrrolidin-1-yl)ethanamine (0.15 ml, 1.15 mmol), EDC (293 mg, 1.53 mmol) and DMAP (cat.) in DMF (5 ml). | O=C(NCCN1CCCC1)c1ccc(CSc2ccc(Cl)cc2NS(=O)(=O)c2ccc(Cl)c(C(F)(F)F)c2)cc1 | null | 71.3 | null |
1,129,350 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[C:9]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22]O)[CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([O:8][CH2:22][CH:19]2[CH2:20][CH2:21][N:16]([C:... | CC(C)(C)OC(=O)N1CCC(CO)CC1 | Oc1ccc(Br)nc1 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | null | null | 1,1-Dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.88 g, 83%) was prepared as a light yellow solid from 2-bromo-5-hydroxypyridine (0.50 g, 2.87 mmol), N-Boc-4-piperidinemethanol (0.64 g, 2.87 mmol) and Ph3P (0.77 g, 2.87 mmol) in THF (15 mL) followed by diisopropyl azodicarboxylate (0.62 ... | CC(C)(C)OC(=O)N1CCC(COc2ccc(Br)nc2)CC1 | null | 82.6 | null |
431,603 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[N:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C[Si]([C:25]#[N:26])(C)C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:11][CH:10]=2)[C:25]#[N:26])=[CH:... | C[Si](C)(C)C#N | COc1ccc(C=Nc2ccc(S(N)(=O)=O)cc2)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 | Following a procedure similar to that described in Example 1(ii), but using N-(4-methoxybenzylidene)-4-sulfamoylaniline [prepared as described in step (i) above] and trimethylsilyl cyanide as starting materials, the title compound was obtained as a pale yellow powder (yield 98%). | COc1ccc(C(C#N)Nc2ccc(S(N)(=O)=O)cc2)cc1 | null | null | null |
1,360,695 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | FC(F)(F)C(O)=O.C[N:9]([CH:11]=[C:12]([N:18]1[CH:22]=[C:21]([C:23]#[N:24])[N:20]=[CH:19]1)[C:13]([O:15]CC)=O)C.[CH:25]1([N:29]2[CH2:34][CH2:33][N:32]([C:35]3[CH:40]=[C:39]([NH:41]N)[N:38]=[CH:37][N:36]=3)[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26]1>C(OCC)(=O)C>[CH:25]1([N:29]2[CH2:34][CH2:33][N:32]([C:35]3[N:36]=[CH:37][... | NNc1cc(N2CCN(C3CCC3)CC2)ncn1 | CCOC(=O)C(=CN(C)C)n1cnc(C#N)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 100 | 20 | 16 μl (23 mg, 0.2 mmol) of trifluoroacetic acid are added to a mixture of 236 mg (1.0 mmol) of the compound from Example 6A and 250 mg (1.0 mmol) of the compound from Example 9A in 4 ml of ethyl acetate, and the mixture is stirred at 100° C. for 20 h. The reaction mixture is concentrated under reduced pressure, more et... | N#Cc1cn(-c2c[nH]n(-c3cc(N4CCN(C5CCC5)CC4)ncn3)c2=O)cn1 | null | null | null |
1,395,996 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[C:14]1[O:18][N:17]=[C:16]([CH3:19])[N:15]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:30])[CH:27]([CH3:29])[CH3:28]>ClCCl>[CH3:12][N:5]1[C:6]2=[N:7][CH:8]=[CH:9][N:10]=[C:11]2[C:2]([O:1][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[C:3]([C:14]2[O:1... | Cc1noc(-c2c(O)c3nccnc3n(C)c2=O)n1 | CC(C)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 8-hydroxy-5-methyl-7-(3-methyl-1,2,4-oxadiazol-5-yl)-5H-pyrido[2,3-b]pyrazin-6-one (Example 7.4) (0.044 g) and pyridine (0.018 ml) in dichloromethane (1 ml) was added dropwise isobutyryl chloride (0.022 ml). The reaction mixture was stirred at ambient temperature for 4 hours and then stored at ambient ... | Cc1noc(-c2c(OC(=O)C(C)C)c3nccnc3n(C)c2=O)n1 | null | null | null |
615,857 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | [NH:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:27])[CH2:24][CH2:25]Cl)=[CH:18][CH:17]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]([NH2:31])([CH3:30])[CH3:29]>>[NH:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH... | O=C(CCCl)Nc1ccc(Nc2ncc(Br)c(Nc3ccccc3)n2)cc1 | CC(C)N | 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 | Using an analogous method to that described in Example 101, but starting from 4-anilino-5-bromo-2-[4-(3-chloropropionamido)anilino]pyrimidine (Method 37) and isopropylamine, the product was obtained. MS (MH+): 469, 471; HPLC (RT): 3.70. | CC(C)NCCC(=O)Nc1ccc(Nc2ncc(Br)c(Nc3ccccc3)n2)cc1 | null | null | null |
112,325 | ord_dataset-5237a168f9214b7ca3db5a1dc3e62d07 | null | 1983-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.C(N(CC)CC)C.[CH2:16](Br)[C:17]#[CH:18]>ClCCl>[CH2:18]([S:8][C:5]1[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=1)[C:17]#[CH:16] | C#CCBr | S=c1ncc(Cl)c[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 1 | A mixture of 5-chloropyrimidine-2-thione (5 mmol) and triethylamine (5 mmol) was stirred together in dichloromethane (40 ml) for 5 min before propargyl bromide (6 mmol) was added. The mixture was stirred at room temperature for 1 h before the solvent was evaporated. The residue was triturated with water (20 ml), and th... | C#CCSc1ncc(Cl)cn1 | null | 87 | null |
1,473,876 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH:27]([CH3:28])[C:26](=[O:29])[NH:25][C:24]4=[O:30])=[N:21][CH:22]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:31]I>>[CH3:1][C:2]1[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([... | CI | Cc1cnc(N2CCN(C(=O)c3ccc(N4C(=O)NC(=O)C4C)nc3)CC2)c(C)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 | Using 1-{5-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-5-methylimidazolidine-2,4-dione (50 mg) described in Example 516 and methyl iodide (9 μL) and by the reaction and treatment in the same manner as in Example 36, the title compound (23 mg) was obtained. | Cc1cnc(N2CCN(C(=O)c3ccc(N4C(=O)N(C)C(=O)C4C)nc3)CC2)c(C)c1 | null | null | null |
597,066 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [CH2:1]([O:8][C@@H:9]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:18].[Na+]>CC(C)=O.C(OCC)C>[CH2:1]([O:8][C@H:9]1[CH2:12][C@H:11]([I:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | [I-] | CS(=O)(=O)O[C@H]1C[C@@H](OCc2ccccc2)C1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A solution of cis-3-benzyloxy-1-methanesulfonyloxycyclobutane (1.25 g, 4.8 mmol) and sodium iodide (2.16 g, 14.4 mmol) in dry acetone (20 ml) was refluxed under nitrogen for 3.5 days. The mixture was cooled and diluted with diethyl ether (150 ml). The suspension was filtered and the filtrate was concentrated. The resid... | I[C@H]1C[C@H](OCc2ccccc2)C1 | null | 86 | null |
1,388,304 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [C:1]([N:5]1[CH:9]=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:17])C(=O)C1.S(=O)(O)[O-].[Na+]>ClCCl>[Br:17][C:8]1[CH:7]=[N:6][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=1 | CC(C)(C)n1cccn1 | O=C1CCC(=O)N1Br | null | O=S([O-])O | [Na+] | 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 | null | To an ice cooled solution (0° C. to 10° C.) of 1-(tert-butyl)pyrazole (1.75 kg, 14.09 mol) in dichloromethane (12.9 kg) was added NBS (2.63 kg, 14.79 mol) portionwise. The solution was stirred at 0° C. until the content of 1-(tert-butyl)pyrazole<30% (GC), then warmed to RT and stirred until the sample taken shows <1.0%... | CC(C)(C)n1cc(Br)cn1 | null | 93.4 | null |
438,361 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].Cl>C(=O)(O)[O-]>[C:11]([C:2]1[N:3]=[C:4]2[C:8]([NH:7][CH:6]=[N:5]2)=[C:9]([NH2:10])[N:1]=1)(=[O:14])[CH:12]=[CH2:13] | C=CC(=O)Cl | Nc1ncnc2nc[nH]c12 | null | Cl | O=C([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 | 1 | Adenine (0.27 g, 0.002 mole) was dissolved in 7 ml of bicarbonate buffer (pH 8), cooled to 0°-4° C., and acrylic acid chloride (1.1 g, 0.01 mole) was added with intense stirring for 1 hour. The solution was acidified with 1 M HCl until pH 6 was obtained, the solvent was evaporated in vacuum and the formed white precipi... | C=CC(=O)c1nc(N)c2[nH]cnc2n1 | null | null | null |
1,074,406 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | O=C1NCCN1C1C=CC([C:13]23[CH2:32][CH:17]4[CH2:18][C:19]([NH:21][CH2:22][C:23]([N:25]5[CH2:29][CH2:28][CH2:27][C@H:26]5[C:30]#[N:31])=[O:24])([CH2:20]2)[CH:15]([CH2:16]4)[CH2:14]3)=CC=1.[Si](Cl)(C)(C)C.[CH3:38][OH:39]>>[O:39]=[C:38]1[CH2:17][CH2:18][CH2:19][N:21]1[C:13]12[CH2:32][CH:17]3[CH2:18][C:19]([NH:21][CH2:22][C:2... | N#C[C@@H]1CCCN1C(=O)CNC12CC3CC1CC(c1ccc(N4CCNC4=O)cc1)(C3)C2 | CO | null | C[Si](C)(C)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 | 0.5 | To a stirred solution of the compound obtained from example 19 (36 mg, 0.1 mmol) in methanol (2 mL) cooled to 0° C. was added TMS-Cl (25 μL, 0.2 mmol). After 30 minutes, the volatiles were removed under reduced pressure and the residue was triturated several times with ether to obtain the hydrochloride salt of (2S)-1-{... | N#C[C@@H]1CCCN1C(=O)CNC12CC3CC1CC(N1CCCC1=O)(C3)C2 | null | null | null |
1,227,224 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:12][CH2:13][CH2:14][C:15](=O)[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=1[NH2:25])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:12][CH2:13][CH2:14]... | COc1cccc(NC(=O)CCCN(C)C(=O)OCc2ccccc2)c1N | null | null | Cc1ccc(S(=O)(=O)O)cc1 | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 150 | null | To a mixture of crude [3-(2-amino-3-methoxy-phenylcarbamoyl)-propyl]methyl-carbamic acid benzyl ester acid in 7 mL toluene were added a few drops of DMF and 523 mg of TsOH and the reaction mixture was heated at 150° C. for 2.5 h in the microwave. Sat. aq. NaHCO3 solution was added, the phases were separated and the org... | COc1cccc2[nH]c(CCCN(C)C(=O)OCc3ccccc3)nc12 | null | null | null |
615,146 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | [OH-].[Na+].[Cl:3][C:4]1[C:13]([CH:14]2[O:18][N:17]=[C:16]([CH3:19])[CH2:15]2)=[C:12]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7].O.Cl.[CH3:26]O>O1CCCC1>[CH3:26][C:11]1[C:12]([S:20]([CH3:23])(=[O:22])=[O:21])=[C:13]([CH:14]2[O:18][N:17]=[C:16]([CH3:19])[CH2:15]2)[C:4]([Cl:3])=[C:5]([CH:10... | CO | COC(=O)c1ccc(S(C)(=O)=O)c(C2CC(C)=NO2)c1Cl | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 12 | 69.4 g (174 mmol) of 10% strength sodium hydroxide solution were added to a solution of 38.4 g (116 mmol) of methyl 2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoate in 400 ml of methanol and 400 ml of tetrahydrofuran. The mixture was stirred for 12 hours at room temperature, the solvent volume wa... | CC1=NOC(c2c(Cl)c(C(=O)O)cc(C)c2S(C)(=O)=O)C1 | null | null | null |
666,329 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](I)[CH3:32]>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:31][CH3:32])[CH2:11][CH2:12][CH2:13][N... | O=C1c2ccccc2C(=O)N1CCCNCCc1ccc(Cl)cc1 | CCI | null | O=C([O-])[O-] | [K+] | 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 | 70 | 16 | To a mixture of N-[3-[2-(4-chlorophenyl)ethylamino]propyl]phthalimide (2.28 g, 6.65 mmol) and potassium carbonate (1.8 g, 13 mmol) in CH3CN (50 ml) was added ethyl iodide (1.6 ml, 20 mmol). The mixture was stirred at 70° C. for 16 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the resi... | CCN(CCCN1C(=O)c2ccccc2C1=O)CCc1ccc(Cl)cc1 | null | 57.2 | null |
149,548 | ord_dataset-f222e615b1f74f0fabef9cd9b98516b7 | null | 1986-01-01T00:10:00 | true | N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>O>[C:16]1([S:22][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH... | CC1NC(=O)NN=C1c1ccc(N)cc1 | Sc1ccccc1 | null | [Na+] | [OH-] | null | 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 | 80 | null | Using 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1 g) in a similar manner to that of Example 18-(1), a diazonium salt-containing aqueous solution was produced. With stirring at 80° C., this solution was added dropwise to a solution composed of thiophenol (1.04 g), sodium hydroxide (0.45 g) and wate... | CC1NC(=O)NN=C1c1ccc(Sc2ccccc2)cc1 | null | 31.6 | null |
272,459 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | [BH4-].[Na+].CN(C)C=O.Cl[C:9](=[O:28])[CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1>O>[OH:28][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C... | O=C(Cl)CCC1CCN(C(=O)OCc2ccccc2)CC1 | null | null | [BH4-] | [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 | null | To a stirred and cooled (ice bath, 10° C.) mixture of 3.4 parts of sodium tetrahydroborate and 188 parts of N,N-dimethylformamide were added dropwise 28 parts of (phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate (exothermic reaction, the temperature rose to 38° C.). Upon completion addition, the reaction ... | O=C(OCc1ccccc1)N1CCC(CCCO)CC1 | null | 61.6 | null |
896,462 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | Cl.[Cl:2][C:3]1[C:12]2[C:11](=[O:13])[NH:10][C@H:9]3[CH2:14][NH:15][CH2:16][C@@H:8]3[C:7]=2[CH:6]=[C:5]([CH2:17][CH3:18])[CH:4]=1.[CH2:19]=O.[BH4-].[Na+]>CO.CCOCC.Cl>[ClH:2].[Cl:2][C:3]1[C:12]2[C:11](=[O:13])[NH:10][C@H:9]3[CH2:14][N:15]([CH3:19])[CH2:16][C@@H:8]3[C:7]=2[CH:6]=[C:5]([CH2:17][CH3:18])[CH:4]=1 | CCc1cc(Cl)c2c(c1)[C@H]1CNC[C@@H]1NC2=O | C=O | null | Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of (3aR,9bS)-6-chloro-8-ethyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one hydrochloride (Example 29) (20 mg, 0.07 mmol) in 2 mL of methanol was added formaldehyde (0.017 mL of 37% aqueous solution, 0.21 mmol) followed by sodium borohydride (14 mg, 0.35 mmol) portionwise. The reaction mixtu... | CCc1cc(Cl)c2c(c1)[C@H]1CN(C)C[C@@H]1NC2=O | null | 142.3 | null |
1,296,735 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[C:17]4[S:21][CH:20](SC)[NH:19][C:18]4=[O:24])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:27]([F:30])([F:29])[F:28])[CH:3]=1.[N:31]1[CH:36]=[C:35]([CH2:37][NH2:38])[CH:34]=[N:33][CH:32]=1>>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:1... | CSC1NC(=O)C(=Cc2ccc3c(cnn3Cc3ccc(Cl)cc3C(F)(F)F)c2)S1 | NCc1cncnc1 | 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-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-[(pyrimidin-5-ylmethyl)-amino]-thiazol-4-one was prepared from 5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-methylsulfanyl-thiazolidin-4-one and C-Pyrimidin-5-yl-methylamine following General Procedure B. | O=C1N=C(NCc2cncnc2)SC1=Cc1ccc2c(cnn2Cc2ccc(Cl)cc2C(F)(F)F)c1 | null | null | null |
1,710,780 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][CH:42]=1)[CH2:6][NH:7][C:8](=[O:39])[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[C:19]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:18]=[CH:17][C:16]=2[NH:27][C:28](=[O:38])[C:29]2([CH2:35][NH:36][CH3:37])[CH:34]=[CH:33][CH:32]=[CH:31][NH:30]2)[... | CNCC1(C(=O)Nc2ccc(N3CCCCC3)cc2-c2cc(C(=O)NCc3cccc(C(F)(F)F)c3)ccn2)C=CC=CN1 | O=C(O)CN1CCOCC1 | 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 | 25 | 4 | Into a 50-mL vial, was placed N-(3-(trifluoromethyl)benzyl)-2-(2-(2-((methylamino)methyl)picolinamido)-5-(piperidin-1-yl)phenyl)isonicotinamide (100 mg, 0.17 mmol, 1.00 equiv) in dichloromethane (10 mL), 2-morpholinoacetic acid (28.9 mg, 0.20 mmol, 1.20 equiv), EDC HCl (47.4 mg, 0.25 mmol, 1.50 equiv), and 4-dimethylam... | CN(CC1(C(=O)Nc2ccc(N3CCCCC3)cc2-c2cc(C(=O)NCc3cccc(C(F)(F)F)c3)ccn2)C=CC=CN1)C(=O)CN1CCOCC1 | null | 93.2 | null |
360,369 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])[CH:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:6][CH2:5]2.[N+:24]([O-])([O-:26])=[O:25].[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[C:10]([N+:24]([O-:26])=[O:25])[CH:11]=1... | CCOC(=O)C(=O)N1C2=CC=C(Br)CC2CCC1CC(=O)OC | O=[N+]([O-])[O-] | null | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(OC(=O)C(F)(F)F)C(F)(F)F | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 1.5 | To a refluxed solution of 6-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline (40 g) and ammonium nitrate (8 g, 0.1 mol) in chloroform (100 mL) was added dropwise trifluoroacetic anhydride (56.5 mL, 0.4 mol) over 40 min. The reflux was continued for 90 min and crashed ice was added. The organic layer was sep... | CCOC(=O)C(=O)N1C2=C([N+](=O)[O-])C=C(Br)CC2CCC1CC(=O)OC | null | 106.7 | null |
732,047 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[S:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1 | Sc1ccccc1 | COc1ccccc1I | 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 general procedure was used to convert 2-iodoanisole and thiophenol to the title product. Purification by flash chromatography (hexane/CH2Cl2 [3:1] as the eluent) gave the analytically pure product as a clear oil (412 mg, 95% yield). 1H NMR (300 MHz, CDCl3) δ 7.41–7.25 (m, 6H; Hc, He, He′, Hf, Hf′, Hg), 7.12 (dd, J=... | COc1ccccc1Sc1ccccc1 | null | null | null |
999,262 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:32]([CH3:34])[CH3:33])[C:15]([C:17]2[CH:25]=[C:24]3[C:20]([C:21]([CH3:31])=[CH:22][N:23]3[CH2:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:19][CH:18]=2)=[O:16])[C@H:10]([CH:35]=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:37]1([NH2:40])[CH2:39][CH2:38]1.[BH-](OC(... | NC1CC1 | COCCCn1cc(C)c2ccc(C(=O)N(C[C@@H]3CN(C(=O)OC(C)(C)C)C[C@H]3C=O)C(C)C)cc21 | 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 | ClCCl | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of (3S,4R)-3-formyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (6 g, 10.9 mmol) in dichloroethane (100 mL), cyclopropylamine (0.85 mL, 12 mmol) and NaBH(OAc)3 (4.32 g, 15.3 mmol) are added. The solution is stirred at RT ... | COCCCn1cc(C)c2ccc(C(=O)N(C[C@@H]3CN(C(=O)OC(C)(C)C)C[C@H]3CNC3CC3)C(C)C)cc21 | null | null | null |
1,517,085 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [Br:1][C:2]1[N:6]([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)[N:5]=[CH:4][CH:3]=1.[OH-].[Na+].CO>O>[Br:1][C:2]1[N:6]([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[N:5]=[CH:4][CH:3]=1 | COC(=O)c1ccc(Cn2nccc2Br)cc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 4 | Methyl 4-((5-bromo-1H-pyrazol-1-yl)methyl)benzoate (264 mg, 0.95 mmol), NaOH (200 mg, 5 mmol) were placed in a 100-mL flask with covered with MeOH and H2O (1:1) and stirred for 4 h at room temperature. The solution was then evaporated, taken up in water and acidified with 2M HCl with the resulting the solid filtered of... | O=C(O)c1ccc(Cn2nccc2Br)cc1 | null | 74.9 | null |
1,738,701 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | FC(F)(F)S(O[C:7]1[C:11]2[C:12]([O:16][CH3:17])=[N:13][CH:14]=[CH:15][C:10]=2[N:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[C:34]([C:37]([O:39][CH3:40])=[O:38])[S:35][CH:36]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2... | COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cs1 | COc1nccc2c1c(OS(=O)(=O)C(F)(F)F)nn2C(C)(C)C | 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 | O | COCCOC | null | null | null | null | null | null | null | null | null | 100 | 8 | To a solution of 1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate (1.60 g) obtained in Step C of Example 86 in DME (100 mL) were added methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (1.46 g) and 2M aqueous sodium carbonate solution (11.3 mL), and then tetrak... | COC(=O)c1cc(-c2nn(C(C)(C)C)c3ccnc(OC)c23)cs1 | null | 120.2 | null |
293,252 | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | null | 1994-01-01T00:07:00 | true | [CH2:1]([O:17][C:18]1[CH:35]=[CH:34][C:21]([O:22][CH2:23][C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:36](OC(=O)C)(=[O:38])[CH3:37].N1C=CC=CC=1>O>[C:36]([N... | CCCCCCCCCCCCCCCCOc1ccc(OCC(=O)NCc2ccccn2)cc1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 110 | null | A mixture of 0.70 g of product from Example 88, 2.96 g of acetic anhydride, 0.027 g of 4-N,N-dimethylaminopyridine and 15 ml of pyridine is heated at 110° C. for 35 hours and at reflux temperature for 57 hours. The reaction is poured into water and extracted with methylene chloride. The organic layer is washed with sat... | CCCCCCCCCCCCCCCCOc1ccc(OCC(=O)N(Cc2ccccn2)C(C)=O)cc1 | null | 48.1 | null |
466,442 | ord_dataset-8cd3720738054d76b936f66e14d8cba6 | null | 2000-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH2:13][CH:14]=C)[C:3]=1[OH:16].C[OH:18]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH2:13][CH2:14][OH:18])[C:3]=1[OH:16] | CO | C=CCc1cc(OC(F)(F)F)cc(Br)c1O | 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 | 25 | 15 | Through a cooled (-78° C.) solution of 2-bromo-6-(prop-2-enyl)-4-trifluormethoxyphenol (Description 15.; 5.9 g, 0.02 mol) in dichloromethane (30 ml) and methanol (30 ml) was bubbled a mixture of ozone in oxygen for 4 h. After the solution had been purged with nitrogen for 1 h., sodium borohydride (0.755 g) was added an... | OCCc1cc(OC(F)(F)F)cc(Br)c1O | null | null | null |
682,457 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:25][C:26]1[C:31]2[CH:32]=[CH:33][O:34][C:30]=2[CH:29]=[CH:28][CH:27]=1.Cl>C(O)(C)C>[O:34]1[C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([NH:25][C:2]3[C... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | Nc1cccc2occc12 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 85 | null | A mixture of 4chloro-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline (0.1 g), 4-aminobenzofuran (0.057 g), isopropanol (4 ml) and a solution of hydrogen chloride in isopropanol (6M, 0.06 ml) was stirred and heated to 85° C. for 3 hours. The resultant mixture was cooled to ambient temperature and the precipit... | COc1cc2c(Nc3cccc4occc34)ncnc2cc1OCCCN1CCN(C)CC1 | null | 109.8 | null |
1,246,798 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[C:4]([Cl:24])[CH:3]=1.[O:25]1[CH2:29][CH2:28][NH:27][C:26]1=[O:30]>>[Cl:24][C:4]1[CH:3]=[C:2]([N:27]2[CH2:28][CH2:29][O:25][C:26]2=[O:30])[CH:7]=[CH:6][C:5]=1[C:8]([N:... | O=C1NCCO1 | Cc1ccc(N2CCN(C(=O)c3ccc(Br)cc3Cl)CC2)c(C)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 | By reaction and treatment in the same manner as in Example 1 and using (4-bromo-2-chlorophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (814 mg) described in Preparation Example 11 and oxazolidin-2-one (174 mg), the title compound (437 mg) was obtained. | Cc1ccc(N2CCN(C(=O)c3ccc(N4CCOC4=O)cc3Cl)CC2)c(C)c1 | null | 52.9 | null |
95,255 | ord_dataset-6f715747ea754945a2f0af4a8482c7d2 | null | 1982-01-01T00:06:00 | true | [CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]3[S:17][CH2:16][CH2:15][CH2:14][N:9]3[C:10](=[O:13])[C:11]=2[CH:12]=1.[OH:19]O>C(O)(=O)C>[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]3[S:17](=[O:19])[CH2:16][CH2:15][CH2:14][N:9]3[C:10](=[O:13])[C:11]=2[CH:12]=1 | OO | CN(C)c1ccc2cc3n(c(=O)c2c1)CCCS3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 1 | A mixture of 550 mg. of 8-dimethylamino-6-oxo-3,4-dihydro-2H,6H-1,3-thiazino[3,2-b]isoquinoline, 10 ml. of acetic acid, and 0.41 ml. of a 35% aqueous hydrogen peroxide solution was stirred at 20°-30° C. After one hour, the reaction mixture was filtered and after adding 10 ml. of water to the filtrate, anhydrous sodium ... | CN(C)c1ccc2cc3n(c(=O)c2c1)CCCS3=O | null | null | null |
1,611,869 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([OH:22])=O)[N:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.[F:23][C:24]([F:33])([F:32])[C:25]1[CH:29]=[C:28]([CH2:30][NH2:31])[O:27][N:26]=1>>[F:33][C:24]([F:23])([F:32])[C:25]1[CH:29]=[C:28]([CH2:30][NH:31][C:20]([C:10]2[N:11]=[N... | NCc1cc(C(F)(F)F)no1 | O=C(O)c1cc(-c2ccc(Cl)cc2)c(OCC(F)(F)F)nn1 | 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 synthesized in analogy to Example 1, using 5-(4-chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridazine-3-carboxylic acid (example M) and 3-trifluoromethyl-isoxazol-5-methanamine (example BA) as starting materials; MS: 480.0 (M)+. | O=C(NCc1cc(C(F)(F)F)no1)c1cc(-c2ccc(Cl)cc2)c(OCC(F)(F)F)nn1 | null | null | null |
1,166,293 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:8]=1)=O.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33]N)=[CH:29][CH:28]=1.Cl>>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:5]([C:7]3[C:12](=[O:13])[CH:11]=[C... | CN(C)/C=C/C(=O)c1nn(-c2cccc(C(F)(F)F)c2)ccc1=O | COc1ccc(NN)cc1 | 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 product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-(3-trifluoromethyl-phenyl)-1H-pyridazin-4-one (A-3) and 4-methoxy-phenylhydrazine×HCl according to the method described for Example 1 in 10% yield. MS: M=413.5 (M+H)+ | COc1ccc(-n2nccc2-c2nn(-c3cccc(C(F)(F)F)c3)ccc2=O)cc1 | null | 10 | null |
1,615,133 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([S:22]([N:25](CC2C=CC(OC)=CC=2OC)[C:26]2[S:30][N:29]=[CH:28][N:27]=2)(=[O:24])=[O:23])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[O:20][CH3:21])#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([S:22]([NH:25][C:26]2[S:30][N:29]=[CH:28... | COc1ccc(CN(c2ncns2)S(=O)(=O)c2ccc(Cc3ccc(C(F)(F)F)cc3OC)c(C#N)c2)c(OC)c1 | 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 | 0 | 3 | 3-Cyano-N-(2,4-dimethoxybenzyl)-4-[2-methoxy-4-(trifluoromethyl)benzyl]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 30, 33.8 mg, 0.056 mmol) was dissolved in dichloromethane (1 mL) and cooled to 0° C. Trifluoroacetic acid (22 μL, 0.28 mmol) was added and the reaction stirred for 3 hours warming slowly to roo... | COc1cc(C(F)(F)F)ccc1Cc1ccc(S(=O)(=O)Nc2ncns2)cc1C#N | null | null | null |
760,558 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]([F:19])=[CH:15][C:16]=1[O:17]C)=[O:10])([O-:3])=[O:2].B(Br)(Br)Br>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]2[CH... | COc1cc(F)c(-c2ccccc2)cc1C(=O)NCc1cccc([N+](=O)[O-])c1 | null | null | BrB(Br)Br | 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 | -78 | 0.75 | A stirring solution of 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid 3-nitro-benzylamide (2.18 g, 5.7 mmol) in dichloromethane (150 mL, 0.4 M) at −78° C. was treated with BBr3 (27 mL, 27 mmol). The mixture was allowed to stir for 45 min at −78° C. and was then quenched with 100 mL of methanol. The mixture was allowed t... | O=C(NCc1cccc([N+](=O)[O-])c1)c1cc(-c2ccccc2)c(F)cc1O | null | 100.6 | null |
76,640 | ord_dataset-8c94910e81cc4281bd57a58ce657576f | null | 1981-01-01T00:02:00 | true | [CH3:1][Mg]I.[CH:4]([C:7]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])([CH3:6])[CH3:5].S(=O)(=O)(O)O>CCOCC>[C:13]([C:7]1([CH:4]([CH3:6])[CH3:5])[CH2:11][CH2:10][CH2:9][C:8]1([CH3:1])[OH:12])([O:15][CH2:16][CH3:17])=[O:14] | C[Mg]I | CCOC(=O)C1(C(C)C)CCCC1=O | null | O=S(=O)(O)O | 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 | Methylmagnesium iodide (0.22 mole) in ether (200 ml.) was added dropwise to a solution of 2-isopropyl-2-carbethoxycyclopentanone (40 g, 0.2 mole) in ether (150 ml.), and the mixture was heated under reflux for 17 hours. Dilute sulphuric acid was then added and the ether layer was separated and dried (MgSO4). The ether ... | CCOC(=O)C1(C(C)C)CCCC1(C)O | null | null | null |
1,367,795 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([F:31])[C:5]([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([F:17])[CH:16]=2)[CH:13]([NH:18][C:19]([C:21]2([NH2:24])[CH2:23][CH2:22]2)=[O:20])[CH2:12][CH2:11]3)[CH:7]=1.[CH3:32][O:33][C:34]1[N:39]=[CH:38][C:37]([C:40](O)=[O:41])=[CH:36][N:35]=1>>[Cl:1][C:... | COc1ncc(C(=O)O)cn1 | Cc1nc(-c2c(F)cc(Cl)cc2-c2cc(F)c3c(c2)CCC3NC(=O)C2(N)CC2)no1 | 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 the procedure described for the preparation of intermediate A-1 [B], 1-amino-cyclopropanecarboxylic acid{(rac)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-7-fluoro-indan-1-yl}-amide (example 32) has been coupled with 2-methoxy-pyrimidine-5-carboxylic acid to yield the title compound as... | COc1ncc(C(=O)NC2(C(=O)NC3CCc4cc(-c5cc(Cl)cc(F)c5-c5noc(C)n5)cc(F)c43)CC2)cn1 | null | null | null |
1,364,941 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]1)=[O:11].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.Cl.[CH3:41][O:42][C:43](=[O:48])[CH:44]([CH2:46][OH:47])[NH2:45]>ClCCl>[CH3:41][O:42][C:43](=[O:48])[CH:44]([CH2:46][OH:47])[NH:45][C:18]([CH:15]1[C... | Cc1ccc(C)c(CC(=O)N2CCC(C(=O)O)CC2)c1 | COC(=O)C(N)CO | null | CCN=C=NCCCN(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN1CCOCC1 | null | null | null | null | null | null | null | null | null | 25 | 0.25 | A mixture of 1-[(2,5-dimethylphenyl)acetyl]-4-piperidinecarboxylic acid (i.e. the product of Example 9, Step B) (1.44 g, 5.23 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.1 g, 5.75 mmol), and N-methylmorpholine (529 mg, 5.23 mmol) in 5 mL of dichloromethane was stirred at room temperature for... | COC(=O)C(CO)NC(=O)C1CCN(C(=O)Cc2cc(C)ccc2C)CC1 | null | null | null |
267,371 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | true | [C:1]([O:6][CH3:7])(=[O:5])[C@H:2]([CH3:4])[OH:3].C(N(CC)CC)C.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[C:15]1([S:21]([O:3][C@@H:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | O=S(=O)(Cl)c1ccccc1 | COC(=O)[C@H](C)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 200g (1.92 mol) of methyl (2S)-lactate (5) and 295 g (2.11 mol) of triethylamine in toluene (1 L) at 0° C. was added 270 mL, 2.11 mol) of benzenesulfonyl chloride dropwise over a 2 hour period under a nitrogen atmosphere. The cooling bath was removed and the reaction mixture was allowed to warm to room... | COC(=O)[C@H](C)OS(=O)(=O)c1ccccc1 | null | 94 | null |
759,153 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | C([O:5][C:6]([C:8]1([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:20]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:21]=4[S:22][CH:23]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[F:30][C:28]([F:29])([F:31])[C:25]1[CH:26]=[CH:27][C:20]2[C:19]([N:16]3[CH2:17][CH2:18][N:13... | CC(C)(C)OC(=O)C1(CCN2CCN(c3csc4cc(C(F)(F)F)ccc34)CC2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | 1-{2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-yl]-ethyl}-cyclopropanecarboxylic acid tert-butyl ester, 0.7 g (1.54 mmol), was stirred in 10 mL of trifluoroacetic acid. After 2 hours the reaction mixture was concentrated to an oil. This was taken up in methanolic hydrogen chloride. The salt thus obtained... | O=C(O)C1(CCN2CCN(c3csc4cc(C(F)(F)F)ccc34)CC2)CC1 | null | null | null |
866,342 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH2:8][O:9]C(=O)C)=[C:4]([CH:15]=O)[CH:3]=1.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][C:23](=[O:27])[NH:24]2)=[CH:20][CH:19]=1.N1CCCC1>CO>[Cl:17][C:18]1[CH:26]=[C:25]2[C:21](/[C:22](=[CH:15]/[C:4]3[CH:3]=[C:2]([Cl:1])[CH:14]=[CH:13][C:5]=3[O:6][CH2:7][CH2:8][OH:9])/[C:23... | O=C1Cc2ccc(Cl)cc2N1 | CC(=O)OCCOc1ccc(Cl)cc1C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNC1 | CO | null | null | null | null | null | null | null | null | null | 70 | null | Acetic acid 2-(4-chloro-2-formyl-phenoxy)-ethyl ester (1.5 g, 9.3 mmol) and 6-chlorooxindole (2.7 g, 11.2 mmol) were mixed in anhydrous methanol (20 mL) at room temperature. Then Pyrrolidine (0.8 g, 11.2 mmol) was added slowly. The reaction mixture was heated at 70° C. for 3 h, then cooled to r.t and the precipitation ... | O=C1Nc2cc(Cl)ccc2/C1=C/c1cc(Cl)ccc1OCCO | null | 43 | null |
864,971 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:24]=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[O:26])[CH:22]=[C:21]([Cl:36])[C:3]=1[C:4]([NH:6][C@H:7]([C:17]([O:19]C)=[O:18])[CH2:8][NH:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[O:11])=[O:5].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([NH:27][CH2... | COC(=O)[C@H](CNC(=O)c1cccs1)NC(=O)c1c(Cl)cc(C(=O)NCc2cccc(O)c2)cc1Cl | null | null | [Na+] | [OH-] | 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 | 25 | 8 | A mixture of N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanine, methyl ester (2.41 g, 4.4 mmol) in methanol (100 Ml) and sodium hydroxide (0.35 g, 8.8 mmol) in water (2 Ml) was stirred at room temperature overnight and then the solvents were evaporated. The r... | O=C(NCc1cccc(O)c1)c1cc(Cl)c(C(=O)N[C@@H](CNC(=O)c2cccs2)C(=O)O)c(Cl)c1 | null | 89 | null |
52,725 | ord_dataset-3d470a6df4a04b1996e024a38c53e818 | null | 1979-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH2:6][CH:7]([C:13]#[N:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:22](OCC)([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]>>[C:8]([C:7]([CH:22]([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])([CH2:6][C:5]1[CH:15]=[C:16]([O:20][CH3:21])[C... | CCOC(OCC)OCC | CCOC(=O)C(C#N)Cc1cc(OC)c(OC)c(OC)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 | A solution of ethyl 3,4,5-trimethoxybenzylcyanoacetate (14.7g) in triethyl orthoformate (100 ml) was heated at reflux for 18 hours using a steam-jacketed column for continuous removal of ethanol. The solution was cooled, and most of the excess orthoformate was removed in vacuo. The crystals obtained were washed with et... | CCOC(=O)C(C#N)(Cc1cc(OC)c(OC)c(OC)c1)C(OCC)OCC | null | 82 | null |
893,952 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [C:1]([C:4]1[N:8]=[CH:7][NH:6][C:5]=1[C:9]#[N:10])(=O)[CH3:2].O.[NH2:12][NH2:13]>C(O)C>[NH2:10][C:9]1[N:13]=[N:12][C:1]([CH3:2])=[C:4]2[N:8]=[CH:7][NH:6][C:5]=12 | CC(=O)c1nc[nH]c1C#N | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 100 | null | A mixture of 2.00 g 5-acetyl-3H-imidazole-4-carbonitrile and 4.00 ml hydrazine hydrate in 50 ml of ethanol is heated to 100° C., until the reaction is complete according to HPLC-MS. After cooling to ambient temperature the reaction mixture is evaporated down, stirred with 20 ml of cold ethanol and suction filtered. The... | Cc1nnc(N)c2[nH]cnc12 | null | null | null |
1,064,380 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | Cl.[Cl:2][C:3]1[CH:16]=[CH:15][C:6]([CH:7]([NH2:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C:17](O)(=[O:28])[CH2:18][NH:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]([NH:14][C:17]([CH2:18][NH:19][C:20](=[O:21])[C:22]2[CH:27]=[CH:26][CH:25]... | NC(c1ccccc1)c1ccc(Cl)cc1 | O=C(O)CNC(=O)c1ccccc1 | 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 | Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and hippuric acid. | O=C(CNC(=O)c1ccccc1)NC(c1ccccc1)c1ccc(Cl)cc1 | null | null | null |
60,460 | ord_dataset-09e9a37ee5794dc28c0ad7bf7a442c18 | null | 1979-01-01T00:11:00 | true | [CH3:1][C:2]1([CH3:24])[C:11](=[O:12])[CH:10]2[C:5](=[C:6]3[N:16]=[C:15]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:14]=[C:7]3[C:8](=[O:13])[CH2:9]2)[CH:4]=[N:3]1.[ClH:25].[O:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][Cl:34])[CH2:28][CH2:27]1>>[ClH:34].[ClH:25].[CH3:1][C:2]1([CH3:24])[C:11](=[O:12])[CH:... | ClCCN1CCOCC1 | CC1(C)N=CC2=C3N=C(Cc4ccccc4)N=C3C(=O)CC2C1=O | 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 | Prepared analogous to Example 23 from 1.6 gm of 7,7-dimethyl-2-benzyl-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione and 1.2 gm of 2-morpholino-ethyl chloride hydrochloride. | CC1(C)N=CC2=C3N=C(Cc4ccccc4)N=C3C(=O)C(CCN3CCOCC3)C2C1=O | null | null | null |
989,756 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[F:28])[CH:10]=2)=[CH:5][CH:4]=1.[CH2:29]([CH2:31][NH2:32])[OH:30]>COCCOC>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:18]... | O=[N+]([O-])c1ccc(Oc2ccnc3cc(-c4ccc(CCl)cc4)sc23)c(F)c1 | NCCO | null | null | null | null | 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 | null | null | To a suspension of the chloride 52 (500 mg, 1.1 mmol) in DME (10 mL) was added ethanolamine (336 mg, 5.5 mmol). The reaction mixture refluxed for 2 hrs, the solvent was removed under reduced pressure; the residue was dissolved in EtOAc and washed with water. The organic phase was collected, dried over sodium sulfate, f... | O=[N+]([O-])c1ccc(Oc2ccnc3cc(-c4ccc(CNCCO)cc4)sc23)c(F)c1 | null | 41.4 | null |
971,590 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | C[O:2][C:3](=[O:27])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:24])([CH3:23])[CH3:22])[C:16]=2[F:25])=[CH:11][C:10]1=[O:26])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1>[F:25][C:16]1[C:17]([C:21]([OH:24])([CH3:22])[CH3:23])=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][C:12]1[CH2:... | COC(=O)[C@H](CC(C)C)N1CC(Oc2cccc(C(C)(C)O)c2F)=CC1=O | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | null | To a solution containing (S)-2-{4-[2-fluoro-3-(1-hydroxy-1-methyl-ethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid methyl ester (2.00 g, 0.005 mol) in tetrahydrofuran (20 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 20 mL, 0.010 mol). The mixture was stirred at ... | CC(C)C[C@@H](C(=O)O)N1CC(Oc2cccc(C(C)(C)O)c2F)=CC1=O | null | 105.6 | null |
1,410,669 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:17]([O:16][C:14](=[O:15])[NH:1][CH:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:10]... | C1CNCCN1 | CC(C)(C)OC(=O)N[C@H](Cc1ccc(Cl)cc1)C(=O)O | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | 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 | 12 | To a solution of Boc-D-Phe(4-Cl)—OH (3.65 g, 12.2 mmol), piperazine (10 g, 116 mmol) in DCM (200 mL) were added HOBT (3.3 g, 24 mmol) and EDCI (4.7 g, 25 mmol). The mixture was stirred at room temperature for 12 hours. The solution was washed with water, brine and dried over magnesium sulfate. After filtration, the org... | CC(C)(C)OC(=O)NC(Cc1ccc(Cl)cc1)C(=O)N1CCNCC1 | null | 12.9 | null |
1,266,994 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:16][OH:17])(C)(C)C>C(Cl)Cl>[NH2:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:16][OH:17] | CC(C)(C)OC(=O)N[C@H](CO)Cc1ccc([N+](=O)[O-])cc1 | 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 | 0.42 | TFA (171 mL) was added to a solution of (S)-tert-butyl-1-hydroxy-3-(4-nitrophenyl)propan-2-ylcarbamate 20 (Erlanson et al., U.S. Pat. No. 7,214,487 B2; 13.9 g, 46.9 mmol) in DCM (272 mL) at 0° C. The reaction mixture was warmed to RT and reaction was allowed to proceed for 25 minutes. The solution was concentrated to a... | N[C@H](CO)Cc1ccc([N+](=O)[O-])cc1 | null | null | null |
724,193 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24].[NH2:25][C:26]1[CH:27]=[CH:28][C:29]2[O:34][CH2:33][CH2:32][S:31](=[O:36])(=[O:35])[C:30]=2[CH:37]=1.Cl>CN1C(=O)CCC1.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[... | Nc1ccc2c(c1)S(=O)(=O)CCO2 | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(S(C)(=O)=O)nc21 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | 120 | null | 83 mg 3-(2-bromo-6-fluorophenyl)-3,4-dihydro-7-methanesulphonyl-1-methyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and 80 mg 6-Amino-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide (starting material h)) in 0.8 ml NMP were treated with 0.2 ml 2M HCl in ether and heated to 120° C. for 6 hrs. From this mixture 21 mg of the title pr... | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(Nc3ccc4c(c3)S(=O)(=O)CCO4)nc21 | null | null | null |
581,547 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[O:11][CH3:12].C(N(CC)CC)C.[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>ClCCl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])=[CH:6][C:5]=1[O:11][CH3:12] | COC(=O)c1ccc(N)cc1OC | CC(C)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 3 | 1.81 g of 4-amino-2-methoxy-benzoic acid methyl ester and 1.4 g of triethylamine were dissolved in 20 ml of dichloromethane. 1.23 g of isobutyryl chloride in 5 ml of dichloromethane was added dropwise at 0° C. The reaction mixture was allowed to reach room temperature and stirred for 3 hours. The reaction mixture was w... | COC(=O)c1ccc(NC(=O)C(C)C)cc1OC | null | 75.7 | null |
528,359 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | CN(C=O)C.[H-].[Na+].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[SH:18].[NH2:19][C:20]1[N:28]=[C:27](Cl)[N:26]=[C:25]2[C:21]=1[N:22]=[CH:23][N:24]2[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>[Cl-].[Na+].O>[NH2:19][C:20]1[N:28]=[C:27]([S:18][C:9]2[CH:10]=[CH:11][C:12]3[C:17](=[... | Nc1nc(Cl)nc2c1ncn2Cc1ccccc1 | Sc1ccc2ccccc2c1 | null | [Cl-] | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 100 | null | To DMF suspension (20 ml) containing sodium hydride (800 mg, 20 mmol, 60% in mineral oil) were added 2-naphthalenethiol (3.8 g, 24 mmol) and 6-amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) in order. The mixture was stirred under heating at 100° C. for 10.5 hours. Brine was added thereto and the mixture was extracte... | Nc1nc(Sc2ccc3ccccc3c2)nc2c1ncn2Cc1ccccc1 | null | 82.6 | null |
818,875 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:6]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=1 | COC(=O)Cc1cccc(C#CCCO[Si](C)(C)C(C)(C)C)c1 | [H][H] | 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 | null | null | A solution of {3-[4-(t-butyidimethylsilyloxy)but-1-ynyl]phenyl}acetic acid methyl ester (700 mg, 2.1 mmol) in MeOH (15 ml) was treated with 5% Pd/C (100 mg) and hydrogen gas (1 atm) for 1 hr. The catalyst was filtered, and the solvent evaporated. The residue was dissolved in THF (1 ml), and treated with tetrabutyl ammo... | COC(=O)Cc1cccc(CCCCO)c1 | null | 64.3 | null |
881,950 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [O:1]=[C:2]1[C:7]([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:6][N:5]=[CH:4][NH:3]1.NN>C(Cl)Cl.CCO>[NH2:9][CH2:8][C:7]1[C:2](=[O:1])[NH:3][CH:4]=[N:5][N:6]=1 | O=C1c2ccccc2C(=O)N1Cc1nnc[nH]c1=O | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCO | null | null | null | null | null | null | null | null | null | 25 | 18 | A slurry of 2-(5-oxo-4,5-dihydro-[1,2,4]triazin-6-ylmethyl)-isoindole-1,3-dione (4 g, 15.6 mmol) in DCM/EtOH (1:1) (150 mL ) was charged with anhydrous hydrazine (1.23 mL, 39.0 mmol) and stirred at rt for 18 h. The reaction mixture was concentrated in vacuo and the off-white solid was triturated with warm CHCl3 and fil... | NCc1nnc[nH]c1=O | null | null | null |
720,548 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [N:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([OH:14])[C:8]([OH:15])=[N:7]2)=[N+:2]=[N-:3].[N+:16]([O-])([OH:18])=[O:17]>C(O)(=O)C>[N:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[N+:16]([O-:18])=[O:17])[N:10]=[C:9]([OH:14])[C:8]([OH:15])=[N:7]2)=[N+:2]=[N-:3] | O=[N+]([O-])O | [N-]=[N+]=Nc1ccc2nc(O)c(O)nc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 24 | 4 | 2 g 6-azido-2,3-dihydroxyquinoxaline is suspended in 100 ml glacial acetic acid. To the suspension is added 16 ml fuming nitric acid at 24° C. The mixture is stirred at 24° C. for 4 h giving a precipitate of 1.9 g (78%) 6-azido-2,3-dihydroxy-7-nitroquinoxaline. IR: a peak at 2120 cm−1. NMR: two singlets (7.0 and 7.7 pp... | [N-]=[N+]=Nc1cc2nc(O)c(O)nc2cc1[N+](=O)[O-] | null | 78 | null |
763,071 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [C:1]([OH:11])(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[I:12](O)(=O)(=O)=O.S(=O)(=O)(O)O.II>O.C(O)(=O)C>[I:12][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][C:1]([OH:11])=[O:10])=[CH:9][CH:8]=1 | [O-][I+3]([O-])([O-])O | O=C(O)CCc1ccccc1 | null | II | O=S(=O)(O)O | 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 | 105 | null | Hydrocinnamic acid is iodinated to form 4-iodohydrocinnamic acid. The process is performed by mixing 201.2 g hydrocinnamic acid, 1 L acetic acid, 152 mL water, 52.8 g periodic acid, 76 mL sulfuric acid, and 144 g iodine. The mixture is heated at 105° C. for 6.5 hours. Next, 200 mL water is added, and the mixture is coo... | O=C(O)CCc1ccc(I)cc1 | null | 460.8 | null |
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