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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
749,962 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([CH2:9][C:10]([OH:12])=O)[C:4]=1[CH3:13])=[O:2].[CH2:14]([N:16]([CH2:19][CH2:20][NH2:21])[CH2:17][CH3:18])[CH3:15]>>[CH2:14]([N:16]([CH2:17][CH3:18])[CH2:19][CH2:20][NH:21][C:10](=[O:12])[CH2:9][C:5]1[C:4]([CH3:13])=[C:3]([CH:1]=[O:2])[NH:7][C:6]=1[CH3:8])[CH3:15] | CCN(CC)CCN | Cc1[nH]c(C=O)c(C)c1CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (5-Formyl-2,4-dimethyl-1H-pyrrol-3-yl)-acetic acid was reacted with diethylaminoethylamine using General Amidation Procedure 1 to give N-(2-diethylamino-ethyl)-2-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-acetamide. MS m/z 280 [M+1]. | CCN(CC)CCNC(=O)Cc1c(C)[nH]c(C=O)c1C | null | null | null |
1,754,982 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:25][CH2:26][CH:27]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:28]([OH:30])=[O:29].C[O-].[Na+].CO.Cl>O>[C:35]([O:34][C:32]([NH:31][C... | CC(C)(C)OC(=O)NC(CN)C(=O)O | COC(=O)c1nc(C#N)c2cc(Oc3ccccc3)ccc2c1O | null | C[O-] | Cl | [Na+] | 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 | 95 | null | A 20-mL scintillation vial was charged with 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.31 mmol), 3-amino-2-tert-butoxycarbonylamino-propionic acid (319 mg, 1.56 mmol) (Bachem) and 0.5 M NaOMe/MeOH solution (2.5 mL, 1.25 mmol). The vial was close capped and heated in a 90-100° C. ... | CC(C)(C)OC(=O)N[C@@H](CNC(=O)c1nc(C#N)c2cc(Oc3ccccc3)ccc2c1O)C(=O)O | null | 71 | null |
309,354 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | [CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:7](=[O:10])[... | O=C(CBr)c1ccccc1 | CCCCc1n[nH]c(=O)n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)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 alkylation of 5-n-butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H- 1,2,4-triazol-3-one (from Example 2, Step D) with phenacyl bromide was carried out as described in Example 3, Step A, except that only 3 equivalents of the alkylating agent was used. After work-up, the residue was flash chro... | CCCCc1nn(CC(=O)c2ccccc2)c(=O)n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | 81 | null |
514,263 | ord_dataset-41760195182e4bb4bc779bd722456071 | null | 2001-01-01T00:08:00 | true | [S-:1][C:2]#[N:3].[Na+].BrBr.[Cl:7][C:8]1[NH:9][C:10]([CH3:15])=[CH:11][C:12]=1[C:13]#[N:14].O>CO>[Cl:7][C:8]1[NH:9][C:10]([CH3:15])=[C:11]([S:1][C:2]#[N:3])[C:12]=1[C:13]#[N:14] | Cc1cc(C#N)c(Cl)[nH]1 | N#C[S-] | null | BrBr | [Na+] | 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 | -78 | 0.5 | A solution of sodium thiocyanate (7.5 g) in 50 ml of methanol was cooled to −76° C. Bromine in 30 ml of cold methanol was added dropwise over 12 min. A slurry of 2-chloro-3-cyano-5-methylpyrrole in 30 ml of cold methanol was added at once. After stirring 30 min at −78° C., the mixture was poured into H2O and stirred ov... | Cc1[nH]c(Cl)c(C#N)c1SC#N | null | null | null |
746,104 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([CH3:12])[N:3]=1.[C:13]([O:17][C:18](=[O:29])[NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)([CH3:16])([CH3:15])[CH3:14]>C(N(CC)C(C)C)(C)C>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([CH... | CC(C)(C)OC(=O)NCCc1ccc(N)cc1 | Cc1cc(Cl)c([N+](=O)[O-])c(Cl)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2,4-dichloro-6-methyl-3-nitro-pyridine (Chorvat, Robert J. et al., J. Med. Chem., 1999, 42, 833., 7.5 g, 36.2 mmol), [2-(4-amino-phenyl)-ethyl]-carbamic acid tert-butyl ester (Stark, Peter A. et al., J. Med. Chem., 1992, 35, 4264., 1.14 g, 4.83 mmol) in N,N-diisopropylethylamine (50 ml) was heated at reflu... | Cc1cc(Nc2ccc(CCNC(=O)OC(C)(C)C)cc2)c([N+](=O)[O-])c(Cl)n1 | null | 15.8 | null |
110,956 | ord_dataset-ac04cf1ba5724e9b93d39b77e9740b21 | null | 1983-01-01T00:11:00 | true | [CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:17]=[N:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=NN=1>C1(C)C=CC=CC=1>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:1... | C=Cc1ccccc1 | Clc1ccccc1-c1nnc(-c2ccccc2Cl)nn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | To styrene (2.34 ml) was added 3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine (2.6 g) in toluene (20 ml). The mixture was heated to reflux for 3 hours, and was then cooled. The solid which separated was filtered off and dried to yield 2.6 g of the desired product, mp 151°-153° C. | Clc1ccccc1C1=NN=C(c2ccccc2Cl)C(c2ccccc2)C1 | null | null | null |
835,039 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:8][O:9][C:10]=2[CH3:11])[N:3]=[CH:2]1.I[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([N:1]2[CH:5]=[C:4]([C:6]3[C:7]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[N:8][O:9][C:... | Cc1onc(-c2ccccc2)c1-c1c[nH]cn1 | COc1ccc(I)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 | As described for Example 2b, 4-(1H-imidazol-4-yl)-5-methyl-3-phenyl-isoxazole (100 mg, 0.44 mmol) using 4-iodoanisole instead of iodobenzene was converted to the title compound (22 mg, 15%) which was obtained as a yellow gum. MS: m/e=332.3 [M+H]+. | COc1ccc(-n2cnc(-c3c(-c4ccccc4)noc3C)c2)cc1 | null | 15 | null |
1,692,288 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | Br[C:2]1[CH:32]=[C:31]([F:33])[C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]3[N:21]=[C:20]([NH:22][C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)[C:19]([O:29][CH3:30])=[CH:18][N:17]=3)=[N:8]2)=[C:4]([F:34])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:40]([O:42][CH2:43][CH3:44])=[CH2:41])CCC.CN1CCCC1=O>C... | COc1cnc(-c2nn(Cc3c(F)cc(Br)cc3F)c3ccccc23)nc1Nc1ccncc1 | C=C(OCC)[Sn](CCCC)(CCCC)CCCC | null | Cl[Pd]Cl | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | 100 | 5 | 100 mg of 2-[1-(4-bromo-2,6-difluorobenzyl)-1H-indazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine (2-12-1, 0.191 mmol, 1 eq.) was suspended in dry toluol. 1.34 mg of dichloropalladium-triphenylphosphane (1:2) (0.002 mmol, 0.01 eq.) and 71 μl of tributyl(1-ethoxyethenyl)stannane (0.21 mmol, 1.2 eq.) were added. T... | C=C(OCC)c1cc(F)c(Cn2nc(-c3ncc(OC)c(Nc4ccncc4)n3)c3ccccc32)c(F)c1 | null | null | null |
789,116 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].[Na]>C(O)C>[CH2:19]([O:18][C:16](=[O:17])/[C:15](/[OH:21])=[CH:11]/[C:10](=[O:12])[C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=1)[CH3:20] | CC(=O)c1ccc(OC(F)(F)F)cc1 | CCOC(=O)C(=O)OCC | null | [Na] | 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 | 0 | 0.5 | A solution of 1-(4-trifluoromethoxy-phenyl)-ethanone (5 g, 24 mmol) and diethyl oxalate (3.25 ml, 24 mmol) in ethanol (5 ml) was added within 20 min to an ice cooled solution of metallic sodium (552 mg, 24 mmol) in ethanol (15 ml) under an argon atmosphere. The cooling bath was removed and the reaction stirred 30 min a... | CCOC(=O)/C(O)=C/C(=O)c1ccc(OC(F)(F)F)cc1 | null | 99.2 | null |
487,654 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | C([NH:4][C:5]1[C:6]([N+:14]([O-:16])=[O:15])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=O)C.S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[NH2:4][C:5]1[C:6]([N+:14]([O-:16])=[O:15])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH2:22][CH3:23])=[O:9] | CCO | CC(=O)Nc1cccc(C(=O)O)c1[N+](=O)[O-] | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 23 | A mixture of 20.2 g of 3-acetylamino-2-nitrobenzoic acid, 11.4 g of 97% sulfuric acid and 300 ml of ethanol was stirred for 23 hours while being heat-refluxed. One-hundred milliliters of ethanol were distilled off under reduced pressure, and the residue was cooled to room temperature. Subsequently, the reaction solutio... | CCOC(=O)c1cccc(N)c1[N+](=O)[O-] | null | null | null |
553,995 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:39]#[N:40])([NH:12][C:13](=[O:38])[CH:14]([NH:22][C:23]([CH:25]2[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]2)=[O:24])[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>Cl.O1CCOCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][C... | CCOC(=O)N1CCC(C#N)(NC(=O)C(CC2CCCCC2)NC(=O)C2CCN(C(=O)OC(C)(C)C)CC2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | The ester from (a) was dissolved in 10 mL of 4 N HCl in 1,4-dioxane at 0° C. for 1 hour. The solution was concentrated in vacuo and the salt neutralized by sodium bicarbonate solution and the product extracted with CH2Cl2. After concentration of the organic extract, the crude product was purified by reverse-phase HPLC ... | CCOC(=O)N1CCC(C#N)(NC(=O)C(CC2CCCCC2)NC(=O)C2CCNCC2)CC1 | null | null | null |
97,556 | ord_dataset-0bf72e95d80743729fdbb8b57a4bc0c6 | null | 1982-01-01T00:08:00 | true | [K].[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.OC1C([C:24]([OH:26])=[O:25])=CC2C(C=1)=CC=CC=2>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:24]([OH:26])=[O:25])[CH:7]=[CH:6]2 | Oc1ccc2ccccc2c1 | O=C(O)c1cc2ccccc2cc1O | null | [K] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In the carboxylation of the potassium salt of 2-hydroxynaphthalene, the initial product form is 3-hydroxy-2-naphthoic acid which subsequently rearranges in situ to form 6-hydroxy-2-naphthoic acid. It has been found that the conditions which favor the formation of 3-hydroxy-2-naphthoic acid in the Kolbe-Schmitt reaction... | O=C(O)c1ccc2cc(O)ccc2c1 | null | null | null |
663,738 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [N:1]1([C:6]([NH2:8])=[NH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:9][C:10]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:11]=1[CH:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15]>>[NH2:17][CH2:16][C:13]1[C:14]([NH2:15])=[N:7][C:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:8][C:12]=1[C:11]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:10]=1[Cl:... | N=C(N)N1CCCC1 | N#CC(C#N)=Cc1ccc(Cl)cc1Cl | null | null | null | null | null | null | null | 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, MS: m/e=337.8 (M+), was prepared from pyrrolidine-1-carboxamidine and 2-(2,4-dichloro-benzylidene)-malononitrile in analogy to the process described in Example 11 as a solid. | NCc1c(N)nc(N2CCCC2)nc1-c1ccc(Cl)cc1Cl | null | null | null |
958,712 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [C:1]([C:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12](=[O:18])[CH2:13][O:14]C(=O)C)[CH2:7][C:6]=2[S:5][C:4]=1[NH:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21])#[N:2].[OH-].[Na+]>>[C:1]([C:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12](=[O:18])[CH2:13][OH:14])[CH2:7][C:6]=2[S:5][C:4]=1[NH:19][C:20](=[O:21])[C:22]1[CH... | CC(=O)OCC(=O)N1CCc2c(sc(NC(=O)c3ccccc3)c2C#N)C1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Acetic acid 2{3-cyano-2-[(1-phenyl-methanoyl)-amino]-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl}-2-oxo-ethyl ester is stirred on 1N NaOH over night at room temperature. Workup as described in general procedure A3 gives the desired product. | N#Cc1c(NC(=O)c2ccccc2)sc2c1CCN(C(=O)CO)C2 | null | null | null |
1,523,229 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [H-].[Na+].[F:3][C:4]([F:34])([F:33])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:10]=[C:9]([NH:19][C:20](=[O:32])[N:21]([CH3:31])[C:22]2[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=2)[N:8]=1.[CH3:35]I>C1COCC1>[CH3:35][N:19]([C:9]1[N:8]=[C:7]([O:6][CH2:5][C:4]([F:3])([F:33... | CN(C(=O)Nc1nc(OCC(F)(F)F)cc(OCC(F)(F)F)n1)c1ccc(C(F)(F)F)s1 | CI | null | [H-] | [Na+] | 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 | 0.17 | To a suspension of NaH (18 mg, 0.36 mmol) in anhydrous THF (3 mL) was added a solution of the 3-(4,6-bis(2,2,2-trifluoro ethoxy)pyrimidin-2-yl)-1-methyl-1-(5-(trifluoromethyl)thiophen-2-yl)urea (2) (150 mg, 0.30 mmol). The reaction was stirred for 10 minutes after which time gas evolution had subsided. To the reaction ... | CN(C(=O)N(C)c1ccc(C(F)(F)F)s1)c1nc(OCC(F)(F)F)cc(OCC(F)(F)F)n1 | null | null | null |
489,898 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | [CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([NH2:13])=[CH:5][CH:4]=[C:3]3[CH2:2]1.C(N(CC)CC)C.[C:21]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>C1(C)C=CC=CC=1>[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([NH:13][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([... | CC(C)(C)c1ccc(CBr)cc1 | Nc1ccc2c3c(cccc13)CC2 | 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 | 4 | null | A mixture of 5-acenaphthylamine (1.0 g, 6 mmol) and triethylamine (0.76 g, 7.5 mmol) in toluene (50 mL) was stirred at 4° C., and 4-tert-butylbenzyl-bromide (1.36 g, 6 mmol) was added in slowly. The reaction mixture was stirred at 23° C. for 15 hours and precipitates formed. The precipitates (triethylamine.HBr) were fi... | CC(C)(C)c1ccc(CNc2ccc3c4c(cccc24)CC3)cc1 | null | null | null |
864,551 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [NH2:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][NH:1][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7] | CCOC(=O)CN | O=C(Cl)c1ccccc1 | 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 | null | null | To a suspension of ethyl 2-amino-acetate (1.0 g, 7.16 mmol) in anhydrous CH2Cl2 (5 ml) was added TEA (1.82 g, 17.96 mmol). The reaction mixture was cooled in an ice bath, and a solution of benzoyl chloride (1.0 g, 7.17 mmol) in CH2Cl2 (2 ml) was added dropwise. After addition was completed, stirring was continued at RT... | CCOC(=O)CNC(=O)c1ccccc1 | null | 83.6 | null |
404,093 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:19]([CH:16]2[CH2:18][CH2:17]2)=[O:20])[CH:6]=[CH:7][CH:8]=1 | O=C(Cl)C1CC1 | Nc1cccc(I)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 5 | 1.53 g of 3-iodoaniline and 2.78 ml of triethylamine are dissolved in 25 ml of methylene chloride and treated dropwise at room temperature with a solution of 1.6 ml of cyclopropane carbonyl chloride in 10 ml of methylene chloride. The mixture is stirred at room temperature for a further 5 hrs., evaporated and poured in... | O=C(Nc1cccc(I)c1)C1CC1 | null | 74 | null |
1,753,110 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH2:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5]([OH:7])=[O:6])[CH2:2][CH3:3].[CH2:11](O)[CH2:12][CH2:13][CH2:14][OH:15]>CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH2:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5]([O:7][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[O:6])[CH2:2][CH3:3] | OCCCCO | CCCC(CCC)C(=O)O | null | CS(=O)(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 2-propylpentanoic acid (40.16 g, 278.5 mmol) was mixed with butane-1-4-diol (114.65 g, 1272.2 mmol) and methyl-sulfonic acid (5 drops) in toluene (3500 ml) and the mixture was heated under reflux using a Dean Stark trap for 12 h. After that, toluene was removed under reduced pressure and the crude mixture was dissolved... | CCCC(CCC)C(=O)OCCCCO | null | 99 | null |
685,672 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.C([O:15][C:16](=O)[CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:26]=[N:27][CH:28]=[N:29][CH:30]=2)[CH:20]=1)(C)(C)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:16](=[O:15])[CH2:17][C:18]([C:19]3[CH:24]=[CH:23... | CC(C)(C)OC(=O)CC(=O)c1cccc(-c2cncnc2)c1 | Nc1cc(Cl)c(Cl)cc1N | null | null | null | 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 | null | The title compound was prepared from commercially available 4,5-dichloro-1,2-phenylendiamine (133 mg, 0.75 mmol) and 3-oxo-3-(3-pyrimidin-5-yl-phenyl)-propionic acid tert-butyl ester (Example K14) (223 mg, 0.75 mmol) in xylene (15 ml) under reflux conditions for 2 h according to the general procedure M. Obtained as a l... | O=C1CC(c2cccc(-c3cncnc3)c2)=Nc2cc(Cl)c(Cl)cc2N1 | null | null | null |
770,460 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2=[C:17]3[C:4]=1[CH2:5][CH:6](O)[N:7]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=1)[C:8]3=[N:9][CH:10]=[N:11]2.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[Br:24][C:20]1[CH:19]=[C:18]([N:7]2[CH:6]=[CH:5][C:4]3[C:17]4[C:8]2=[N:9][CH:10]=[N:11][C:12]=4[CH:13]=[C:14]([O:1... | COc1cc2ncnc3c2c(c1OC)CC(O)N3c1cccc(Br)c1 | null | null | CS(=O)(=O)Cl | 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 | 2 | To a solution of 7,8-dimethoxy-4-(3-bromo-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol (0.17 g, 0.42 mmol) (from Example 22, Step A, supra) and triethylamine (0.35 mL, 2.53 mmol) in dichloromethane (30 mL) at 0° C. was added methanesulfonyl chloride (0.13 mL, 1.68 mmol) (Aldrich). The reaction solution was stirred... | COc1cc2ncnc3c2c(c1OC)C=CN3c1cccc(Br)c1 | null | null | null |
1,461,123 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][N:2]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]4[CH3:35])=[C:25]([C:36]([F:39])([F:38])[F:37])[CH:24]=3)[O:20][N:19]=2)[CH:15]=[CH:14][N:13]=1)[CH2:3][C:4]([O:6]C(C)(C)C)=[O:5].Cl>O1CCOCC1>[CH3:1][N:2]([CH2:11][C:12]1[CH:17]=[C:... | CC1CCCCN1c1ccc(-c2nc(-c3ccnc(CN(C)CC(=O)OC(C)(C)C)c3)no2)cc1C(F)(F)F | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 70 | 4 | To tert-butyl 2-(methyl((4-(5-(4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methyl)amino)acetate (0.056 g; 0.10 mmol) was added HCl solution in dioxan (4 M; 3 mL) and the reaction mixture stirred at 70° C. for 4 hours. The solvent was evaporated in vacuo and the residue purifi... | CC1CCCCN1c1ccc(-c2nc(-c3ccnc(CN(C)CC(=O)O)c3)no2)cc1C(F)(F)F | null | null | null |
1,075,049 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([NH:24][C@H:25]([CH2:29][CH3:30])[C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16... | CC1(C)CNCC[C@]1(O)c1ccc(Cl)cc1 | CC[C@@H](NC(=O)OC(C)(C)C)C(=O)O | null | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (100 mg, 0.42 mmol), (R)-2-(tert-butoxycarbonylamino)butanoic acid (102 mg, 0.50 mmol), HOBT (68 mg, 0.5 mmol), EDC (155 mg, 1 mmol), DIPEA (129 mg, 1 mmol), and chlororform (2 mL) was stirred overnight at rt. The reaction mixture was then partitioned between methylene ... | CC[C@@H](NC(=O)OC(C)(C)C)C(=O)N1CC[C@](O)(c2ccc(Cl)cc2)C(C)(C)C1 | null | null | null |
1,346,194 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>C1COCC1>[Br:45][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:8]=[... | OCc1ccc(-c2ncn(-c3ccc(OC(F)(F)F)cc3)n2)cc1 | BrC(Br)(Br)Br | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 23 | To a solution of {4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-methanol (P-6; 5.033 g, 15.01 mmol) in THF (100 mL) was added triphenylphosphine (6.009 g, 22.91 mmol). Carbon tetrabromide (7.704 g, 23.23 mmol) dissolved in THF (20 mL) was then added dropwise at room temperature. The mixture was allowe... | FC(F)(F)Oc1ccc(-n2cnc(-c3ccc(CBr)cc3)n2)cc1 | null | 77.1 | null |
1,595,661 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][CH3:15])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(N2CCC(F)(F)C2)C2N=NNC=2N=1)(C)(C)C.ClC[C:45]1[CH:50]=[CH:49][CH:48]=C[C:46]=1[O:51][CH3:52]>>[C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C:18]([... | CCn1nnc2c(N3CCC(F)(F)C3)nc(C(C)(C)C)nc21 | COc1ccccc1CCl | null | CC(C)(C)c1nc(N2CCC(F)(F)C2)c2nn[nH]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 | In analogy to the procedure described for the synthesis of 5-tert-butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 61), the title compound was prepared from 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 1-(chloromethyl)-2-methoxybenzene a... | COc1ccccc1Cn1nnc2c(N3CCC(F)(F)C3)nc(C(C)(C)C)nc21 | null | null | null |
171,839 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[Cl:13]N1C(=O)CCC1=O>>[NH2:1][C:2]1[C:3]([Cl:13])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6] | COC(=O)c1ccc(Cl)c(N)c1 | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This material was prepared by chlorination of methyl 3-amino-4-chlorobenzoate with N-chlorosuccinimide. The product was isolated as a solid, mp 50°-52° C. The product was characterized by IR and 1H NMR spectroscopy and combustion analysis. | COC(=O)c1ccc(Cl)c(N)c1Cl | null | null | null |
1,185,135 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | C([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH:15]=2)=[CH:9][C:8]=1[Cl:30])C.[OH-].[Na+].Cl>C(O)C>[Cl:30][C:8]1[CH:9]=[C:10]([S:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([C:21]#... | CCOC(=O)COc1ccc(Sc2cc(O)cc(C#Cc3ccc(Cl)cc3)c2)cc1Cl | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 1 | {2-Chloro-4-[3-(4-chloro-phenylethynyl)-5-hydroxy-phenylsulfanyl]-phenoxy}-acetic acid ethyl ester (50 mg; 0.11 mmol) was dissolved in ethanol (6 mL), and aqueous 1 N sodium hydroxide (3 mL) was added. The reaction mixture was stirred for 1 h, acidified with 1 N aqueous hydrochloric acid, and extracted with ethyl aceta... | O=C(O)COc1ccc(Sc2cc(O)cc(C#Cc3ccc(Cl)cc3)c2)cc1Cl | null | null | null |
377,714 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)[CH2:8][CH2:7]1)=[O:5])C.[ClH:22]>>[ClH:22].[CH2:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][CH:12]1[N:9]1[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1 | CCOC(=O)C1CCN(C2CCc3ccccc3C2)CC1 | null | 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 | 8 | Ethyl-1-(tetralin-2-yl)piperdine-4-carboxylate (7.1 g, 0.025 mol) was treated with 6N HCl (80 ml) at room temperature. After stirring overnight, the suspension was filtered off and the solid dried in vacuo to yield 1-(tetralin-2-yl)piperdine-4-carboxylic acid hydrochloride salt. | O=C(O)C1CCN(C2CCc3ccccc3C2)CC1 | null | null | null |
255,465 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [Na].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5](Cl)[N:4]=1.[CH2:13]([OH:16])[CH2:14][CH3:15]>>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5]([O:16][CH2:13][CH2:14][CH3:15])[N:4]=1 | CCCO | Nc1nc(Cl)c2[nH]cnc2n1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 85 | null | Sodium (0.68 g, 29.5 mmol Aldrich lot #9621CL) was added in portions to anhydrous propanol (25 mL). Upon complete dissolution 2-amino-6-chloropurine (1 g, 5.9 mmol, Sigma lot #69F4064) was added and the reaction heated in an 85° C. oil bath under a nitrogen atmosphere for 20 hours. The solution was cooled and neutraliz... | CCCOc1nc(N)nc2nc[nH]c12 | null | null | null |
1,005,395 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([C:19]#[N:20])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1>CO.N>[NH2:20][CH2:19][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH:17]=[CH:18][C:9]([NH:8][CH2:7][C:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)=[N:10]2 | Cc1ccc(CNc2ccc3c(C#N)cccc3n2)o1 | null | null | N | 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 | Hydrogenation of 2-[(5-methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbonitrile (200 mg, 0.76 mmol) dissolved in 7N MeOH—NH3 for 23 h at room temperature yielded after removal of the catalyst by filtration and evaporation a yellow oil which was further purified by column chromatography (dichloromethane/MeOH/NH4OH 15:1:... | Cc1ccc(CNc2ccc3c(CN)cccc3n2)o1 | null | 97.5 | null |
879,264 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [CH:1]([CH:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[C-:11]#[N:12].[Na+]>>[CH:1]([CH:3]([C:11]#[N:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2] | [C-]#N | C=CC(Cl)c1ccccc1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | a procedure according to A. Zerroukhi, A. Ainser, A. Arsac, N. Mignard, and B. Marculescu, Polymer Bulletin, 42, 535, 1999, is used. Initially, vinylbenzyl chloride is reacted with sodium cyanide to give vinylbenzyl cyanide, which is then reacted with ethanolamine to give the vinylbenzyloxazoline. | C=CC(C#N)c1ccccc1 | null | null | null |
138,475 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | Cl[C:2]1[N:3]=[C:4]2[C:9](=[N:10][C:11]=1[N:12]1[CH2:17][CH2:16][S:15][CH2:14][CH2:13]1)[N:8]=[C:7]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[N:6]=[C:5]2[N:24]1[CH2:29][CH2:28][S:27][CH2:26][CH2:25]1.[CH2:30]([OH:32])[CH3:31]>>[CH2:30]([O:32][C:2]1[N:3]=[C:4]2[C:9](=[N:10][C:11]=1[N:12]1[CH2:17][CH2:16][S:15][CH... | Clc1nc2c(N3CCSCC3)nc(N3CCNCC3)nc2nc1N1CCSCC1 | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared analogous to Example 3 from 6-chloro-2-piperazino-4,7-bis-(thiomorpholino)pteridine and ethanol. | CCOc1nc2c(N3CCSCC3)nc(N3CCNCC3)nc2nc1N1CCSCC1 | null | null | null |
1,116,545 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][CH2:17][F:18].[H-].[Na+].O>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([O:11][CH2:16][CH2:17][F:18])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3] | CC(=O)c1cc(O)cc(C(C)(C)C)c1 | FCCBr | null | [H-] | [Na+] | null | 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 | null | 8 | 1-(3-tert-Butyl-5-hydroxyphenyl)ethanone (O3.106; 500 mg) was dissolved in DMF (10 ml), and 1-bromo-2-fluoroethane (195 μl) was added while stirring. Sodium hydride (80 mg) was added at RT. After stirring at RT for 3 h, the mixture was left to stand overnight and then further sodium hydride (20 mg) was added and the mi... | CC(=O)c1cc(OCCF)cc(C(C)(C)C)c1 | null | null | null |
980,615 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:17](OC)(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[SH:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:16][CH:10]([CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:1]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24]... | CCOC(=O)C(C)Cc1cccc(C#N)n1 | COC(=O)c1ccccc1S | 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 | null | null | Ethyl 3-(6-cyano-2-pyridyl)-2-methylpropionate (0.79 g, 3.6 mmol) and methyl thiosalicylate (1.2 g, 7.3 mmol) were dissolved in toluene (3 ml), and triethylamine (0.76 ml, 5.4 mmol) was added thereto. The reaction mixture was refluxed for 21 hrs and subjected to a silica gel (70 g) column chromatography. The fractions ... | CCOC(=O)C(C)Cc1cccc(-c2nc(=O)c3ccccc3s2)n1 | null | 69.8 | null |
1,017,478 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[S:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[N:20]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27]>N1C=CC=CC=1>[N:20]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[S:13][C... | COc1cc(C(=O)Cl)cc(OC)c1OC | COC(=O)c1cc(N)cc(-c2nc3ccncc3s2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | Methyl 3-amino-5-(thiazolo[5,4-c]pyridin-2-yl)benzoate (150 mg, 0.526 mmol) was mixed together with 3,4,5-trimethoxybenzoyl chloride (121 mg, 0.526 mmol) in 1 mL of pyridine. The reaction mixture was reacted in a Biotage microwave reactor at 160 degrees for 10 min. It was then cooled to room temperature and concentrate... | COC(=O)c1cc(NC(=O)c2cc(OC)c(OC)c(OC)c2)cc(-c2nc3ccncc3s2)c1 | null | 35.7 | null |
462,196 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][NH:15][C:1... | COC(=O)CCCCCCCCc1ccc2cccnc2n1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 20 | A mixture of 13-3 (8.5 g, 28 mmol), 10% Pd/C (1.7 g), and ethanol (140 mL) was stirred under a hydrogen atmosphere for 20 h. The reaction mixture was then filtered through a celite pad and concentrated to give 13-4 as a pale yellow oil. | COC(=O)CCCCCCCCc1ccc2c(n1)NCCC2 | null | null | null |
929,392 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]1([N:25]2[C:29](=[S:30])[N:28]=[N:27][NH:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]([OH:42])[CH2:39][CH2:40]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Cl:31][C:32]1[CH:37]=[CH:36][CH:35... | S=c1nn[nH]n1-c1cccc2ccccc12 | OCCC(O)c1ccccc1Cl | null | CC(C)OC(=O)/N=N/C(=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 | 25 | 2 | DIAD (82 μL, 0.42 mmol) was added dropwise to a solution of 1,2-dihydro-1-(1-naphthalenyl)-5H-tetrazole-5-thione (80.0 mg, 0.35 mmol), 1-(2-chlorophenyl)-1,3-propanediol (65.4 mg, 0.35 mmol), and PPh3 (110 mg, 0.42 mmol) in THF (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h th... | OC(CCSc1nnnn1-c1cccc2ccccc12)c1ccccc1Cl | null | 50.4 | null |
905,882 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][NH:13][CH2:12][C@@H:11]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[C:31]([O:33][C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)=[O:32]>C1COCC1>[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:11]... | CC(C)(C)[Si](C)(C)OC[C@H]1CNC[C@@H]1c1cccnc1 | COC(=O)c1ccc(OC(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 3 | 3-[(3S,4R)-4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyrrolidin-3-yl]pyridine and N,N-diisopropylethylamine were dissolved in THF, methyl 4-[(chlorocarbonyl)oxy]benzoate (mfd. by Fluka) was added in one portion thereto at room temperature and stirred for 3 hours, and then the reaction solution was concentrated under a ... | COC(=O)c1ccc(OC(=O)N2C[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](c3cccnc3)C2)cc1 | null | null | null |
978,512 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | C1(O[C:8](=[O:25])[NH:9][CH:10]2[CH2:15][CH2:14][C:13]([N:22]([CH3:24])[CH3:23])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)C=CC=CC=1.[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[C:30]2[CH:36]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]1>O1CCOCC1>[CH3:24][N:22]([CH3:23])[C:13]1... | Fc1ccc2[nH]cc(C3CCCNC3)c2c1 | CN(C)C1(c2ccccc2)CCC(NC(=O)Oc2ccccc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | The polar diastereoisomer of (4-dimethylamino-4-phenylcyclohexyl)-carbamic acid phenyl ester (338 mg, 1 mmole) was added to a solution of 5-fluoro-3-piperidine-3-yl-1H-indole (218 mg, 1 mmole) in dioxane (10 ml). The reaction mixture was then boiled under reflux for 32 hours. The reaction mixture was worked up by disti... | CN(C)C1(c2ccccc2)CCC(NC(=O)N2CCCC(c3c[nH]c4ccc(F)cc34)C2)CC1 | null | null | null |
1,254,314 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:27])[NH:17][C:18]1[N:19]=[C:20]2[N:24]([CH:25]=1)[CH:23]=[C:22](Br)[S:21]2)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:35][O:36][C:37](=[O:70])[NH:38][C@H:39]([C:43]([N:45]1[CH2:49]... | CC(C)(C)OC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1cn2cc(Br)sc2n1)c1ccccc1 | COC(=O)N[C@H](C(=O)N1CCC[C@H]1c1ncc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)[nH]1)C(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 | Compound A38 was synthesized from compound 23 (0.091 mmol) and compound 8 (0.137 mmol), following the procedure as described for compound A1 (reaction time=1 hr), as a white lyophilized powder in 10% yield. MS (ESI, EI+) m/z=838.39 (MH+). | COC(=O)N[C@H](C(=O)N1CCC[C@H]1c1ncc(-c2ccc(-c3cn4cc(NC(=O)[C@@H]5CCCN5C(=O)[C@@H](NC(=O)OC(C)(C)C)c5ccccc5)nc4s3)cc2)[nH]1)C(C)C | null | 10 | null |
81,550 | ord_dataset-f196f0a87dd74fcd82ca019f8ff5cf9c | null | 1981-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[O:5][CH:6]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:23])[N:15]([CH2:17][CH:18](OC)[O:19]C)[CH3:16])=[N:10][N:9]=1)[CH3:7]>O.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[O:5][CH:6]([C:8]1[S:12][C:11]([N:13]2[CH:18]([OH:19])[CH2:17][N:15]([CH3:16])[C:14]... | COC(CN(C)C(=O)Nc1nnc(C(C)Oc2ccc(Cl)c(Cl)c2)s1)OC | null | null | Cl | 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 | null | null | A solution containing 4.0 grams of the 3-[5-[1-(3,4-dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-(2,2-dimethoxyethyl)urea (prepared above) in 200 milliliters of water and 2 milliliters of concentrated hydrochloric acid (HCl) was refluxed for 165 minutes, cooled and then extracted with chloroform CHCl3, and ph... | CC(Oc1ccc(Cl)c(Cl)c1)c1nnc(N2C(=O)N(C)CC2O)s1 | null | 109 | null |
626,691 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [C:1]1([C:7]2[N:8]=[CH:9][O:10][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([NH:18][NH2:19])=[N:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31]>ClCCl>[C:1]1([C:7]2[N:8]=[CH:9][O:10][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([NH:18][NH:19][C:29](=[O:33])[CH:30]([CH3:32])[... | NNc1ccc(-c2ocnc2-c2ccccc2)cn1 | 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(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 0 | 2 | To a solution of 5-(4-Phenyl-oxazol-5-yl)-pyridin-2-yl-hydrazine (2.5 g, 9.9 mmol), and N,N-diisopropylethylamine (8.6 mL, 50 mmol) in dichloromethane (8 mL) at 0° C. was added dropwise isobutyryl chloride (1.04 mL, 9.9 mmol); the mixture was stirred at 0° C. for 2 hours. The reaction was quenched with water and extrac... | CC(C)C(=O)NNc1ccc(-c2ocnc2-c2ccccc2)cn1 | null | null | null |
856,543 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [OH:1][CH:2]1[CH2:5][N:4]([C:6](=[O:8])[CH3:7])[CH2:3]1.N12CCCN=C1CCCCC2.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([O:1][CH:2]1[CH2:5][N:4]([C:6](=[O:8])[CH3:7])[CH2:3]1)([C:21]1[CH:26]=[CH:25][... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | CC(=O)N1CC(O)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | In 50 mL of methylene chloride was dissolved 10.0 g of 1-(3-hydroxy-1-azetidinyl)-1-ethanone, and 31.2 mL of 1,8-diazabicyclo[5,4,0]undec-7-ene and 29.1 g of trityl chloride were added thereto under ice-cooling, after which the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poure... | CC(=O)N1CC(OC(c2ccccc2)(c2ccccc2)c2ccccc2)C1 | null | 69.9 | null |
1,597,088 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH:1]12[CH2:7][NH:6][CH:5]1[CH2:4][N:3](C1C=NC3C(=CC=CC=3)N=1)[CH2:2]2.Cl[C:19]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:21][N:20]=1>>[C:25]1([C:23]2[CH:22]=[CH:21][N:20]=[C:19]([N:3]3[CH2:4][CH:5]4[CH:1]([CH2:7][NH:6]4)[CH2:2]3)[N:24]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1 | c1ccc2nc(N3CC4CNC4C3)cnc2c1 | Clc1nccc(-c2ccccc2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner analogous to Intermediate 8, using 2-chloro-4-phenyl pyrimidine. MS (ESI) mass calcd. for C15H16N4, 252.31; m/z found 253.2 [M+H]+. | c1ccc(-c2ccnc(N3CC4CNC4C3)n2)cc1 | null | null | null |
1,453,487 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH3:1][C:2]1([CH3:10])[O:7][CH:6]([CH2:8][OH:9])[CH2:5][O:4][CH2:3]1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][S:12]([O:9][CH2:8][CH:6]1[CH2:5][O:4][CH2:3][C:2]([CH3:10])([CH3:1])[O:7]1)(=[O:14])=[O:13] | CS(=O)(=O)Cl | CC1(C)COCC(CO)O1 | null | O=C([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 | 1 | TEA (0.52 mL, 3.74 mmol) and (6,6-dimethyl-1,4-dioxan-2-yl)methanol (390 mg, 2.67 mmol) were dissolved in DCM (10 mL). Methanesulfonyl chloride (0.249 mL, 3.20 mmol) was slowly added at 0° C. After the addition was completed the solution was warmed to ambient temperature and stirred for 1 hr. Saturated NaHCO3 solution ... | CC1(C)COCC(COS(C)(=O)=O)O1 | null | 97.5 | null |
1,280,482 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [O:1]=[C:2]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][N:10](C(OC)=O)[C@@H:9]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:8]2)[O:4][NH:3]1.Br>>[F:26][C:23]([F:24])([F:25])[C:20]1[CH:19]=[CH:18][C:17]([C@H:9]2[CH2:8][C@H:7]([C:5]3[O:4][NH:3][C:2](=[O:1])[CH:6]=3)[CH2:12][CH2:11][NH:10]2)... | COC(=O)N1CC[C@@H](c2cc(=O)[nH]o2)C[C@@H]1c1ccc(C(F)(F)F)cc1 | null | 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 | 25 | 8 | Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)phenyl)piperidine-1-carboxylate (148 mg, 0.40 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 3 mL, 17.13 mmol) and the solution stirred at room temperature overnight. The solvent was evaporated and the residue purified by preparative HP... | O=c1cc([C@@H]2CCN[C@@H](c3ccc(C(F)(F)F)cc3)C2)o[nH]1 | null | 40 | null |
365,016 | ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | null | 1997-01-01T00:05:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[O:13]>>[OH:13][CH:12]([CH:2]([CH3:3])[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])[C:11]([O:15][CH2:16][CH3:17])=[O:14] | CCOC(=O)C=O | CCC(=O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 135 | null | A mixture of 13.4 g of propiophenone and 15.3 g of ethyl glyoxylate is heated at 135° C. for 5 hours. | CCOC(=O)C(O)C(C)C(=O)c1ccccc1 | null | null | null |
626,217 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [C:1]1([C:7]2[C:15](C)=[C:14]([C:17]([O-:19])=O)[CH:13]=[CH:12][C:8]=2[C:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.[CH2:21]1COCC1>C1COCC1>[CH3:21][O:11][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][C:14]([CH2:17][OH:19])=[CH:15][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | C1CCOC1 | Cc1c(C(=O)[O-])ccc(C(=O)[O-])c1-c1ccccc1 | null | B | null | null | null | 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 | 0.5 | To a 0° C. solution in THF (40 mL) of 2-phenylmonomethylterephthalate (10.5 g, 41 mmol) was added borane-THF (1.0 M, 82 mL, 82 mmol) such that the reaction temperature remained below 6° C. The reaction mixture was stirred for 0.5 hours, then the cold bath was removed and stirring was continued for 2 hours. The reaction... | COC(=O)c1ccc(CO)cc1-c1ccccc1 | null | 98.2 | null |
685,240 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:18]([O-:20])=[O:19])[CH:12]=[C:13]([CH:17]=2)[C:14]([O-:16])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K+].[K+]>O>[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:18]([OH:20])=[O:19])[CH:12]=[C:13]([CH:17]=2)[C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=C([O-])c1cc(C#Cc2ccccc2)cc(C(=O)[O-])c1 | null | null | [K+] | 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 | null | null | Dipotassium 5-(2-phenylethynyl)isophthalate in an amount of 6.5 g (0.019 moles) was dissolved into 20 ml of ion-exchanged water and insoluble substances were removed by filtration with a 5C filter paper. To the obtained filtrate, a 5 moles/liter hydrochloric acid was added under stirring until the pH became 1. The form... | O=C(O)c1cc(C#Cc2ccccc2)cc(C(=O)O)c1 | null | 99.5 | null |
1,561,436 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [F:1][C@H:2]1[C@@H:7]([OH:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.CC([O-])(C)C.[K+].C1COCC1.[N:30]1[N:31]=[C:32]([C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[C:42](F)[CH:43]=[CH:44][CH:45]=3)[N:40]=2)[N:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=12>CN(C=O)C>[N:3... | Fc1cccc2ccc(-c3nnc4ccccn34)nc12 | O=C(OCc1ccccc1)N1CC[C@H](O)[C@H](F)C1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | Non-racemic (cis)-benzyl 3-fluoro-4-hydroxypiperidine-1-carboxylate (Peak 1 of Example 94, Step 3D; 0.288 g, 1.14 mmol) was treated with 1.0 M KOtBu in THF (1.10 mL, 1.10 mmol) and stirred at ambient temperature for 15 minutes. 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-fluoroquinoline (0.200 g, 0.757 mmol) was added as ... | O=C(OCc1ccccc1)N1CC[C@H](Oc2cccc3ccc(-c4nnc5ccccn45)nc23)[C@H](F)C1 | null | null | null |
41,521 | ord_dataset-48929f64ce614f1181a555eafd7c97a6 | null | 1978-01-01T00:06:00 | true | [C:1]1([C:7]2[C:13]3[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[S:21])[CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:24][N:25]([CH2:27][CH2:28]Cl)[CH3:26].O>CN(C)C=O>[CH3:24][N:25]([CH3:26])[CH2:27][CH2:28][S:21][C:10]1[CH2:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH... | O=[N+]([O-])c1ccc2c(c1)C(c1ccccc1)=NCC(=S)N2 | CN(C)CCCl | null | [H-] | [Na+] | null | 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 | 25 | 0.25 | To a solution of 11.4 g of 1,3-dihydro-5-phenyl-7-nitro-2H-1,4-benzodiazepin-2-thione in 140 ml of anhydrous dimethylformamide is added under ice cooling with stirring 3.6 g of sodium hydride (50% oily suspension), and the resulting mixture is stirred at room temperature for 15 minutes. To this mixture is added dropwis... | CN(C)CCSC1=Nc2ccc([N+](=O)[O-])cc2C(c2ccccc2)=NC1 | null | null | null |
839,875 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [F:1][C:2]([F:7])([CH2:5][OH:6])[CH2:3][OH:4].[CH2:8]([O:15][CH2:16][CH:17]=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:8]([O:15][CH2:16][CH:17]1[O:6][CH2:5][C:2]([F:7])([F:1])[CH2:3][O:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1 | OCC(F)(F)CO | O=CCOCc1ccccc1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2,2-difluoropropane-1,3-diol (1 g, 8.9 mmol), benzyloxyacetaldehyde (1.34 g, 8.9 mmol), p-toluenesulfonic acid monohydrate (154 mg, 0.81 mmol) and toluene (20 ml) was heated under reflux by a condenser equipped with a Dean-Stark apparatus for one hour. The resultant mixture was stirred at room temperature ... | FC1(F)COC(COCc2ccccc2)OC1 | null | 42.8 | null |
112,086 | ord_dataset-5237a168f9214b7ca3db5a1dc3e62d07 | null | 1983-01-01T00:12:00 | true | [NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@@H:2]([C:12]([OH:14])=O)[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[NH2:25][C@H:26]([C:30]([NH:32][C@H:33]([C:46]([O:48][CH3:49])=[O:47])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]([CH3:45])([CH3:44])[CH3:4... | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OCc1ccccc1)C(=O)O | COC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)[C@@H](N)C(C)C | null | Cl | null | 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 | null | 4.04 g (12 mmoles) of Z-D-Glu(OBut)-OH are subjected to a condensation reaction with 4.64 g (12 mmoles) of H-Val-Tyr(But)-OMe.HCl in 25 ml of dimethylformamide analogously to Example 38 A. Yield 6.72 g. The substance is purified further by chromatography on silica gel. The eluting agent is a mixture of methylene chlori... | COC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)[C@@H](NC(=O)[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OCc1ccccc1)C(C)C | null | null | null |
999,710 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]([O:13][C:14](=[O:35])[N:15]([C:17]1[CH:25]=[C:24]2[C:20]([CH:21]=[CH:22][N:23]2[CH2:26][C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=2)=[CH:19][CH:18]=1)[CH3:16])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])O.[Na+]>ClCCl.C(OCC)C>[C:9]([O:13][C:14](=[O:35... | CN(C(=O)OC(C)(C)C)c1ccc2ccn(Cc3cc(F)cc(F)c3)c2c1 | Sc1ccccc1Br | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.25 | —Sulfuryl chloride (1.08 ml, 13.4 mmol) was added to a solution of 2-bromobenzenethiol (1.27 g, 6.69 mmol) in dichloromethane (45 ml). The reaction mixture was stirred at room temperature for 15 min. and concentrated under reduced pressure. The resulting material was dissolved in diethyl ether and added dropwise to a s... | CN(C(=O)OC(C)(C)C)c1ccc2c(Sc3ccccc3Br)cn(Cc3cc(F)cc(F)c3)c2c1 | null | 80.7 | null |
874,183 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | B1(C2C=CC(O)=CC=2)O[C:4](C)(C)[C:3](C)(C)O1.[OH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:28]=[CH:27][O:26][C:25]=2[C:29]([OH:31])=[O:30])=[CH:20][CH:19]=1>>[OH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:28]=[CH:27][O:26][C:25]=2[C:29]([O:31][CH2:3][CH3:4])=[O:30])=[CH:20][CH:19]=1 | O=C(O)c1occc1-c1ccc(O)cc1 | CC1(C)OB(c2ccc(O)cc2)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 | Using 4-hydroxyphenylboronic acid pinacol cyclic ester, a reaction and treatment was carried out in the same manner as in Reference Example 2, thereby giving 3-(4-hydroxyphenyl)-2-furancarboxylic acid. A reaction and treatment was further carried out in the same manner as in Reference Example 1, thereby giving the desi... | CCOC(=O)c1occc1-c1ccc(O)cc1 | null | null | null |
742,324 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=4[Cl:26])=[CH:15][C:13]=3[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:27]1[C:32]([C:33]([OH:35])=[O:34])=[CH:31][C:30]2[C:36]([O:38][C:39](=O)[C:29]=2[CH:28]=1)=[O:37]>>[CH3:9][O:8][C:7]1[CH:6]=[CH:5... | COc1ccc(-c2nc3cc(-c4cccc(Cl)c4Cl)ccc3o2)cc1N | O=C(O)c1ccc2c(c1)C(=O)OC2=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by the method of Example 1b), from 2-(3-amino-4-methoxyphenyl)-5-(2,3-dichlorophenyl)benzoxazole (238 mg, 0.60 mmol) and 1,2,4-benzenetricarboxylic anhydride (119 mg, 0.60 mmol) the title compound was obtained (191 mg, 57%). 1H NMR (DMSO) δ 8.46(dd, 1H), 8.35(m, 3H), 8.13(d, 1H), 7.84(m, 2H), 7.70(m, 1H), 7.47... | COc1ccc(-c2nc3cc(-c4cccc(Cl)c4Cl)ccc3o2)cc1N1C(=O)c2ccc(C(=O)O)cc2C1=O | null | null | null |
1,622,665 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | P(Br)(Br)([Br:3])=O.[CH:6]1([C:9]2[C:10](=[O:20])[N:11]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[CH:12]=[CH:13][C:14]=2O)[CH2:8][CH2:7]1>CN(C=O)C>[Br:3][C:14]1[CH:13]=[CH:12][N:11]([CH2:16][CH:17]2[CH2:19][CH2:18]2)[C:10](=[O:20])[C:9]=1[CH:6]1[CH2:8][CH2:7]1 | O=P(Br)(Br)Br | O=c1c(C2CC2)c(O)ccn1CC1CC1 | null | null | null | 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 | 110 | null | Phosphorus oxybromide (2.4 g, 8.28 mmol) was added to a solution of intermediate D35 (0.85 g, 4.14 mmol) in DMF (60 ml), and the mixture was heated at 110° C. for 1 hour. After cooling in an ice bath, the solution was partitioned between water and EtOAc. The mixture was extracted with EtOAc (3×200 ml), the combined org... | O=c1c(C2CC2)c(Br)ccn1CC1CC1 | null | null | null |
788,016 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([S:38][CH2:39][C:40]5[N:44]([CH2:45][CH3:46])[N:43]=[N:42][N:41]=5)=[CH:34][CH:33]=4)=[O:30])=[CH:20][C:19]=3[CH:47]=2)=[CH:... | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(SCc4nnnn4CC)cc2)CCN3CC(C)C)cc1 | O=C(OO)c1cccc(Cl)c1 | null | O=S([O-])([O-])=S | [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 | null | 0.25 | To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[(1-ethyl-tetrazol-5-yl)methyl]sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (0.45 g) in methylene chloride (13.5 ml) was added dropwise a solution of m-chloroperbenzoic acid (0.12 g) in methylene chloride (9.0 ml) at −78° C., and the mixture was... | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(S(=O)Cc4nnnn4CC)cc2)CCN3CC(C)C)cc1 | null | 47.9 | null |
904,931 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=[N:21][OH:22])[CH:18]([CH3:20])[CH3:19])=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C[Si]([N:27]=[C:28]=[O:29])(C)C.N1C=CC=CC=1>C1COCC1>[C:28]([O:22][N:21]=[C:17]([C:16]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][N:10]2[CH:15]=... | CC(C)C(=NO)c1c(-c2ccc(F)cc2)nn2ccccc12 | C[Si](C)(C)N=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 48 | To a solution of 742 mg (2.5 mmol) of 1-(2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime in 5 ml of anhydrous THF was added 2 ml of trimethylsilyl isocyanate (85%) dropwise at 0° C. over 30 minutes. The mixture was stirred at room temperature over 48 hours, followed by addition of 50 μl pyridi... | CC(C)C(=NOC(N)=O)c1c(-c2ccc(F)cc2)nn2ccccc12 | null | 56.7 | null |
1,656,218 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][N:16]=[N:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=... | Brc1ccnnc1 | NCc1ccc(B(O)O)cc1 | 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 | CCO | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 110 | 2 | To a sealed tube was added 4-(aminomethyl)phenylboronic acid 1-1 (1.87 g, 10 mmol), 4-bromopyridazine 1-2 (1.58 g, 10 mmol), Pd(PPh3)4 (230 mg, 0.2 mmol), saturated Na2CO3 (15 mL), ethanol (15 mL) and toluene (45 mL). The reaction was heated to 110° C. and stirred for 2 hours. The reaction was cooled down to room tempe... | NCc1ccc(-c2ccnnc2)cc1 | null | null | null |
1,531,902 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [Si]([O:8][CH2:9][C:10]1([CH3:40])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:34]=[CH:33][C:32]([C:35]([N:37]([CH3:39])[CH3:38])=[O:36])=[CH:31][CH:30]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO>[OH:8][CH2:9][C:10]1([CH3:40])[S:16][C... | CN(C)C(=O)c1ccc(-c2ccc(C3(c4nnc5n4CCSC(C)(CO[Si](C)(C)C(C)(C)C)C5)CC3)cc2)cc1 | null | null | Cl | 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 the compound (318 mg, 0.55 mmol) obtained in Example 6-1) and 4 M hydrochloric acid (1,4-dioxane solution, 0.69 mL) in methanol (2 mL) was stirred at room temperature for 21 h. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate was added to the residue... | CN(C)C(=O)c1ccc(-c2ccc(C3(c4nnc5n4CCSC(C)(CO)C5)CC3)cc2)cc1 | null | 55 | null |
1,696,441 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | CO[C:3]([C:5]1[C:6]([OH:34])=[C:7]2[C:12](=[C:13]([C:15]3[S:19][CH:18]=[N:17][CH:16]=3)[N:14]=1)[N:11]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10](=[O:27])[C:9]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:8]2)=[O:4].[NH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39].C[O-].[Na+]>C([O-])(O)=O.[Na+]>... | NCCC(=O)O | COC(=O)c1nc(-c2cncs2)c2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | C[O-] | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-8-thiazol-5-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (61 mg, 0.13 mmol), β-alanine (695 mg, 7.8 mmol) and NaOMe solution (11.7 mL, 5.9 mmol, 0.5 M in MeOH) was refluxed for 16 h. After the mixture was cooled to r.t., the solvent was evaporated in va... | O=C(O)CCNC(=O)c1nc(-c2cncs2)c2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | 40.9 | null |
1,104,995 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)(=O)C>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33... | O=C(Cl)c1ccccc1 | COc1ccc(-c2nc(N)sc2Cc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 8 | To a 100 ml three-necked flask were added 0.50 g (1.69 mmol) 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1, 1.42 g (10.12 mmol) triethylamine and 40 ml ethyl acetate, and then added dropwise 0.48 g (3.38 mmol) benzoyl chloride dissolved in 10 ml ethyl acetate. The resulting mixture was magnetica... | COc1ccc(-c2nc(NC(=O)c3ccccc3)sc2Cc2ccccc2)cc1 | null | 57.6 | null |
908,246 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | I[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:37])[C:35]#[CH:36])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.ClCCl.CO.N>>[Cl:20][C:21]1[CH:22]=[CH:23][C:... | C#CC(=O)Nc1ccc(-c2ccc(Cl)cc2)cc1 | Ic1ccc(CN2CCC(N3CCCC3)CC2)cc1 | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 1.1.d. from 1-(4-iodobenzyl)-4-pyrrolidin-1-ylpiperidine and propynoic acid-(4′-chlorobiphenyl-4-yl)amide. Yield: 15 mg (7% of theory); melting point: 191° C.-192° C.; C31H32ClN3O (M=498.07); calc.: molecular ion peak (M+H)+: 498/500; found: molecular ion peak (M+H)+: 498/500; Rf value: ... | O=C(C#Cc1ccc(CN2CCC(N3CCCC3)CC2)cc1)Nc1ccc(-c2ccc(Cl)cc2)cc1 | null | null | null |
1,414,201 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [C:1]([C:3]1[C:4]([CH3:20])=[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1)#N.CC(C[AlH]CC(C)C)C.ClCCl.[O:33]1CCCC1>>[CH:1]([C:3]1[C:4]([CH3:20])=[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1)=[... | Cc1c(C#N)cccc1NC(=O)OCc1ccccc1 | C1CCOC1 | null | CC(C)C[AlH]CC(C)C | 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 | To a solution of benzyl 3-cyano-2-methylphenylcarbamate (6.41 g, 24.07 mmol) in tetrahydrofuran (250 mL) at −78° C. was added DIBAL-H in dichloromethane (96 mL, 96 mmol) over 1 hr. The mixture was stirred at −78° C. for 45 min and then at room temperature for 5 hr. It was poured into ice cold water (300 mL) and the res... | Cc1c(C=O)cccc1NC(=O)OCc1ccccc1 | null | 87 | null |
738,159 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH:12]([O:16][CH3:17])[C:13]([OH:15])=O.[NH2:18][CH2:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1>>[C:19]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:13](=[O:15])[CH:12]([C:3]2[CH:4]=[C:5]([O:10][CH3:11])[C:6]([O:8][CH3:9])=[... | COc1cc(F)c(C(OC)C(=O)O)cc1OC | N#Cc1ccc(CN)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 | (RS)-(2-Fluoro-4,5-dimethoxy-phenyl)-methoxy-acetic acid was coupled with 4-aminomethyl benzonitrile according to general procedure B to give (RS)-N-(4-cyano-benzyl)-2-(2-fluoro-4,5-dimethoxy-phenyl)-2-methoxy-acetamide. Red foam. MS 359.2 ([M+H]+) | COc1cc(F)c(C(OC)C(=O)NCc2ccc(C#N)cc2)cc1OC | null | null | null |
751,742 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([F:16])[C:5](/[CH:8]=[N:9]/[S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[N:6][CH:7]=1.[CH3:17][Mg]Cl.O>C(Cl)Cl.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([C@H:8]([NH:9][S:10]([C:12]([CH3:13])([CH3:15])[CH3:14])=[O:11])[CH3:17])=[N:6][CH:7]=1 | CC(C)(C)S(=O)/N=C/c1ncc(Br)cc1F | C[Mg]Cl | null | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of N-[(1E)-(5-bromo-3-fluoropyridin-2-yl)methylidene]-2-methyl-propane-2-sulfinamide (18.63 g, 60.65 mmol) in CH2Cl2 (375 mL) was cooled to −50° C. under N2. Methylmagnesium chloride (3M in THF, 30.32 mL, 90.97 mmol) was added dropwise, the reaction was stirred for 1 h. Additional methylmagnesium chloride (5... | C[C@@H](NS(=O)C(C)(C)C)c1ncc(Br)cc1F | null | null | null |
966,182 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[CH3:13]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[CH3:11])[C:5]([O:7][CH3:13])=[O:6] | Cc1c(Cl)cc(C(=O)O)cc1Cl | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared in the same manner as in Reference Example 1 (step 1), except that 3,5-dichloro-4-methylbenzoic acid (Japanese Unexamined Patent Publication (Kokai) No. 6-192196) was used and methanol was used as the solvent, and that the crude product was purified by silica gel column chromatography. | COC(=O)c1cc(Cl)c(C)c(Cl)c1 | null | null | null |
371,676 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | C(OC([NH:11][CH:12]([CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1)=[O:14])=O)C1C=CC=CC=1.[CH:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][C:37]=1[S:46](Cl)(=[O:48])=[O:47]>[Pd... | CCOC(=O)Cc1ccc(NC(=O)C(COC2CCCCO2)NC(=O)OCc2ccccc2)cc1 | O=S(=O)(Cl)c1ccc2ccccc2c1 | null | [Pd] | null | null | null | null | null | 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 procedure described in Example 15 was repeated, except that (RS)-2-(benzyloxycarbonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-3-(tetrahydropyran-2-yloxy)propanamide (500 mg) was hydrogenolyzed in the presence of 10% Pd-C, and then, reacted with 2-naphthalenesulfonyl chloride (463 mg) to obtain (RS)-N-(4-(ethoxycar... | CCOC(=O)Cc1ccc(NC(=O)C(COC2CCCCO2)NS(=O)(=O)c2ccc3ccccc3c2)cc1 | null | 62 | null |
716,384 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[C:2]=[O:3].[NH2:10][C@H:11]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:21]=[C:22]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH:23]=[CH:24][CH:25]=2)[CH2:16][CH2:15]1>>[NH:1]([C:2]([NH:10][C@H:11]([C:32]... | CC(C)C(=O)Nc1cccc(C2CCN(CC[C@H](N)c3ccccc3)CC2)c1 | O=C=Nc1ccccc1 | null | null | null | null | null | null | null | 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 by Procedure P and Scheme AB using isocyanatobenzene and N-(3-{1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide: ESMS m/e: 499.2 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CC[C@H](NC(=O)Nc3ccccc3)c3ccccc3)CC2)c1 | null | null | null |
1,458,474 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[O:13]1CCC[CH2:14]1>>[O:13]=[C:14]1[NH:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[NH:1]1 | C1CCOC1 | COC(=O)c1cccc(N)c1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 15 | To a suspension of methyl 2,3-diaminobenzoate (32.9 g, 198 mmol) in tetrahydrofuran (300 mL) was added N,N′-carbonyldiimidazole (33.7 g, 208 mmol), and the mixture was stirred at room temperature for 15 hr. The solvent was evaporated in vacuo, and the residual solid was suspended in ethyl acetate (110 mL) and stirred a... | COC(=O)c1cccc2[nH]c(=O)[nH]c12 | null | 94 | null |
1,213,672 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]2)=[C:4]([O:14][CH3:15])[CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([CH:27]=[C:28]([F:31])[C:29]=1[F:30])[CH2:20][N:21]1[CH:25]=[N:24][C:23]([NH2:26])=[N:22]1>>[CH3:15][O:14][C:4]1[CH:3]=[C:2]([NH:26][C:23]2[N:24]=[CH:25][N:21]([CH2:20][C:19]3[CH:27]=[C:28]... | COc1cc(Br)ccc1-n1cnc(C)c1 | Nc1ncn(Cc2cc(F)c(F)c(F)c2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogy to example 1b) starting with 1-(4-bromo-2-methoxy-phenyl)-4-methyl-1H-imidazole (WO2009076352) and 1-(3,4,5-trifluoro-benzyl)-1H-[1,2,4]triazol-3-ylamine from example 17a). The title compound was obtained as a colorless foam (Yield=49%). MS ISP (m/e): 415.2 (100) [(M+H)+]. | COc1cc(Nc2ncn(Cc3cc(F)c(F)c(F)c3)n2)ccc1-n1cnc(C)c1 | null | null | null |
1,763,548 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17](O)=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1.[CH3:25][C:26]1[O:30][C:29]([C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)=[N:28][N:27]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:... | CCC(C(=O)O)n1cc(OC)c(-c2cc(Cl)ccc2C#N)cc1=O | Cc1nnc(-c2ccc(N)cc2)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 mg (0.29 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 76 mg (0.43 mmol, 1.5 eq.) of 4-(5-methyl-1,3,4-oxadiazol-2-yl)aniline were reacted according to General Method 7. The crude product was purified by normal phase chromatography (mobile phase: dichloromethane... | CCC(C(=O)Nc1ccc(-c2nnc(C)o2)cc1)n1cc(OC)c(-c2cc(Cl)ccc2C#N)cc1=O | null | null | null |
10,114 | ord_dataset-53cd7fd33c6f4f1c804e187bec94be57 | null | 1976-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:12]=O>OS(O)(=O)=O>[CH3:12][NH:4][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[CH3:1] | C=O | Cc1cc([N+](=O)[O-])ccc1N | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | 0.17 | 15.2 g of 2-methyl-4-nitroaniline were dissolved in 150 ml conc. H2SO4 and heated in a boiling water bath. To this solution 24 g. of paraformaldehyde were added with stirring over a period of 10 minutes. The mixture was stirred an additional hour and was then cooled and poured over 300 g of ice. The precipitate was rec... | CNc1ccc([N+](=O)[O-])cc1C | null | null | null |
93,099 | ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2 | null | 1982-01-01T00:04:00 | true | [CH2:1]([O:3][C:4](=[O:16])[C:5](=[CH2:15])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:15][O:25]1)=[O:16])[CH3:2] | O=C(OO)c1cccc(Cl)c1 | C=C(CCCc1ccccc1)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 1 | 10 g of 5-phenyl-2-methylenevaleric acid ethyl ester and 18.3 g of m-chloroperbenzoic acid (85% pure) are boiled under reflux in 180 ml of methylene chloride for 40 hours. The mixture is allowed to cool; the m-chloroperbenzoic acid (which has separated out) is filtered off; the filtrate is concentrated; the residue is ... | CCOC(=O)C1(CCCc2ccccc2)CO1 | null | 77.3 | null |
681,618 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.Br[C:24]1[N:28]2[N:29]=[CH:30][C:31]([C:33]([F:36])([F:35])[F:34])=[N:32][C:27]2=[N:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C... | FC(F)(F)c1cnn2c(Br)cnc2n1 | CC1(C)OB(c2ccc(F)c(-c3cccnc3)c2)OC1(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 | COCCOC | null | null | null | null | null | null | null | null | null | null | null | null | 3-[2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine (151 mg, 0.51 mmol) was coupled to 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.09 g, 0.34 mmol) as described in Example 37, step e, using 2 M Na2CO3 (0.51 ml) and tetrakis(triphenylphosphine)palladium(0) (0.019 g) in 1,2-dimethoxy... | Fc1ccc(-c2cnc3nc(C(F)(F)F)cnn23)cc1-c1cccnc1 | null | 44.2 | null |
476,153 | ord_dataset-d56f0a7ec215495c92e641d9fa932d28 | null | 2000-01-01T00:09:00 | true | [CH3:1][C:2]1[N:6]2[C:7]3[C:12]([NH:13][C:14](=O)[C:5]2=[N:4][CH:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C[Si](C)(C)N[Si](C)(C)C.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[CH:32]1([NH:37]C2CCCC2)[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([NH:37][C:14]2[C:5]3[N:6]([C:2]([CH3:1])=[CH:3][N:4]=3)[C:7]3[C:12]([N:13]=2)=[CH:11][CH:10]=... | Cc1cnc2c(=O)[nH]c3ccccc3n12 | C1CCC(NC2CCCC2)C1 | null | C[Si](C)(C)N[Si](C)(C)C | O=S(=O)([O-])[O-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 120 | 24 | A mixture of 3.5 g of 1-methylimidazo[1,2-a] quinoxalin-4(5H)-one (example 2), 13 ml of hexamethyl disilazane, 0.5 g of ammonium sulphate and 8.7 ml dicyclopentylamine is stirred at 120° C. in a Dean-Stark apparatus for 24 h. After concentrating the resulting mixture under vacuum, the residue is added with water and ex... | Cc1cnc2c(NC3CCCC3)nc3ccccc3n12 | null | null | null |
1,412,019 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:7]2[CH:11]=[CH:10][NH:9][N:8]=2)[S:5][CH:6]=1.[I:12]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]2[C:11]([I:12])=[CH:10][NH:9][N:8]=2)[S:5][CH:6]=1 | Clc1csc(-c2cc[nH]n2)c1 | O=C1CCC(=O)N1I | null | O=C([O-])[O-] | O=S([O-])([O-])=S | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 3-(4-chloro-2-thienyl)-1H-pyrazole (24.0 mmol) was dissolved in 50 mL N,N-dimethylformamide under argon atmosphere. N-Iodosuccinimide (25.1 mmol) was added in small portions. The reaction mixture was stirred at room temperature overnight. 5% aqueous sodium thiosulfate solution and saturated aqueous sodium carbonate sol... | Clc1csc(-c2n[nH]cc2I)c1 | null | 91.2 | null |
142,008 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | [CH3:1][Li].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([NH:13][C:14]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](O)=[O:27])(=[O:19])=[O:18])=[O:15])[N:6]=1.Cl>CCOCC.O1CCCC1>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([O:4][CH3:3])[N:6]=[C:7]([NH:13][C:14]([NH:16][S:17]([C:20]2[CH:25]=[CH:24]... | [Li]C | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | null | 4 | A methyllithium solution in ether (1.4M, 40 ml) was added to a solution of 1.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamide in 50 ml of dry tetrahydrofuran at room temperature. The resulting yellow slurry was stirred for 4 hours and the dilute hydrochloric acid was added. The mixture ... | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2C(C)=O)n1 | null | null | null |
1,652,030 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([C:17](OCC)=[O:18])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1>O1CCCC1>[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1 | CCOC(=O)C1CCC2(CC1)OCCO2 | null | null | [Al+3] | [H-] | [Li+] | 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 | 2 | To a suspension of lithium aluminum hydride (8.19 g) in tetrahydrofuran (400 mL) was added dropwise a solution of EXAMPLE 341A (37.8 g) in tetrahydrofuran (75 mL). The mixture was then heated at reflux for 2 hours. The reaction mixture was cooled in an ice bath and quenched very slowly with water (8 mL). Then added seq... | OCC1CCC2(CC1)OCCO2 | null | null | null |
1,496,582 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]([F:12])([F:11])[CH2:9]I.[F:13][C:14]1[CH:42]=[CH:41][CH:40]=[CH:39][C:15]=1[CH2:16][N:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[C:19]([C:26]2[N:27]=[C:28]([OH:38])[C:29]3[C:34]([CH3:36])([CH3:35])[C:33](=[O:37])[NH:32][C:30]=3[N:31]=2)=[N:18]1>CN(C=O)C>[F:13][C:14]1[CH:42]=... | FC(F)(F)CI | CC1(C)C(=O)Nc2nc(-c3nn(Cc4ccccc4F)c4ncccc34)nc(O)c21 | null | O=C([O-])[O-] | [Cs+] | 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 | 25 | 8 | 177 mg (0.54 mmol) of caesium carbonate and 114 mg (0.54 mmol) of 2,2,2-trifluoroethyl iodide were added to a suspension of 200 mg (0.5 mmol) of the compound from example 109 in DMF (1.97 ml) and it was stirred overnight at RT. Then it was heated in the microwave to 120° C. for 1 h. The reaction mixture was purified by... | CC1(C)C(=O)Nc2nc(-c3nn(Cc4ccccc4F)c4ncccc34)nc(OCC(F)(F)F)c21 | null | null | null |
1,762,535 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][O:2][N:3]=[C:4]([C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=1)[CH2:5]Br.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.O>C(#N)C>[CH3:1][O:2][N:3]=[C:4]([C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=1)[CH2:5][NH:18][CH:15]1[CH2:17][CH2:16]1 | NC1CC1 | CON=C(CBr)c1ncc(Cl)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | 25 | 18 | To 700 mg of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-methyloxime prepared in the same manner as in Steps 1 to 3 in Synthetic Example 2 in 10 ml of acetonitrile, 402 mg of cyclopropylamine in 5 ml of acetonitrile was added, and the mixture was stirred at room temperature for 18 hours. After completion of the reac... | CON=C(CNC1CC1)c1ncc(Cl)cc1Cl | null | 69.9 | null |
616,031 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | COC(=O)[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C:13]([N:15]1[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][C@H:16]1[CH3:30])=[O:14].[N+:32](C1C=C(Cl)C=CC=1O)([O-:34])=[O:33].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC.O>[Cl:10][C:8]1[CH:7]=... | COC(=O)c1cc(Cl)ccc1OCC(=O)N1C[C@H](C)N(Cc2ccc(F)cc2)C[C@H]1C | O=[N+]([O-])c1cc(Cl)ccc1O | null | O=C([O-])[O-] | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of (2R, 5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoic acid methyl ester (1.0 g, 3.35 mmol) in butanone (35 ml) was added 2-nitro-4-chlorophenol (0.639 g, 3.69 mmol), potassium carbonate (0.925 g, 6.7 mmol) and potassium iodide (0.556 g, 3.35 mmol). The reaction ... | C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-] | null | 92.5 | null |
186,870 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | CN([CH:9]=[O:10])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[CH:16]1[C:33]2[C:20](=[CH:21][C:22]3[C:31]([CH:32]=2)=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=3)[CH:19]=[CH:18][CH:17]=1>ClC1C=CC=CC=1Cl>[CH:19]1[C:20]2[C:33](=[C:32]([CH:9]=[O:10])[C:31]3[C:22]([CH:21]=2)=[CH:23][C:24]2[C:29](=[CH:28][CH:27]=[CH:26][C... | c1ccc2cc3cc4ccccc4cc3cc2c1 | CN(C=O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | Clc1ccccc1Cl | null | null | null | null | null | null | null | null | null | 25 | 12 | To a 3-necked RB flask equipped with overhead mechanical stirrer, condenser, addition funnel, N2 inlet line with bubbler was added n-methylformanilide (Aldrich 89.21 g, 0.66 mol, 81 mL) and o-dichlorobenzene (Aldrich, 200 mL). The mixture was cooled to 10° with an ice bath. Phosphorus oxychloride (Aldrich, 101.21 g, 0.... | O=Cc1c2ccccc2cc2cc3ccccc3cc12 | null | 31 | null |
417,416 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [OH:1][C:2]1([CH3:40])[CH:26]=[C:25]2[C@:20]([CH3:38])([CH2:21][CH2:22][C@H:23]([O:27][Si](C(C)C)(C(C)C)C(C)C)[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:39])([CH2:17][CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.N#N>>[OH:27][C@H:2... | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C(C)C)(C(C)C)C(C)C)CC1=CC3(C)O | null | null | CCCC[N+](CCCC)(CCCC)CCCC | N#N | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of methyl 7-hydroxy-7-methyl-3β-triisopropylsilyloxychol-5-en-24-oate (6) (4.67 g, 8.22 mmoles) and tetrabutylammonium fluoride (1.0M in THF, 49 ml) was heated at 65° in a N2 atmosphere for 30 min. Most of the THF was removed in vacuo. The residue was dissolved in EtOAc (90 ml) and washed with H2O (two times)... | COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3(C)O | null | 60.4 | null |
1,014,231 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[N:18]=[CH:19][C:20]=2[CH:21]([CH3:23])[CH3:22])=[CH:10][C:9]=1[CH3:32])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:37]>CN(C=O)C>[C:1]([O:5][C:6](=[O:33])[N:7]([C:8]1[CH:13]... | Cc1cc(OCc2c(C(C)C)cnn2-c2c(Cl)cccc2Cl)ccc1NC(=O)OC(C)(C)C | CI | 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 | 0.5 | To a 0° C. solution of {4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-carbamic acid tert-butyl ester (1.9 g, 3.9 mmol) in DMF (15 mL) is added sodium hydride (60% dispersion in mineral oil, 0.19 g, 4.7 mmol) portionwise. The mixture is stirred at 0° C. for 30 minutes. Iodomethane (0.83... | Cc1cc(OCc2c(C(C)C)cnn2-c2c(Cl)cccc2Cl)ccc1N(C)C(=O)OC(C)(C)C | null | 94 | null |
923,745 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)([O-])=O>[Pd].C(O)C>[N:16]1[CH:17]=[CH:18][C:13]([C:9]2[N:8]([CH2:7][C:6]3[CH:5]=[C:4]([NH2:1])[CH:21]=[CH:20][CH:19]=3)[CH:12]=[CH:11][N:10]=2)=[CH:14][CH:15]=1 | O=[N+]([O-])c1cccc(Cn2ccnc2-c2ccncc2)c1 | 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 | 4 | Ethanol (20 mL) is added to 4-[1-(3-Nitro-benzyl)-1H-imidazol-2-yl]-pyridine (730 mg, 2.6 mmol) and 10% palladium on charcoal (100 mg) under an atmosphere of argon. The atmosphere is purged 3 times with H2 on a Parr shaker type hydrogenation apparatus, and the mixture is shaken for 4 h at 50 psi H2. The mixture is filt... | Nc1cccc(Cn2ccnc2-c2ccncc2)c1 | null | null | null |
568,723 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]2[N:14]=[C:15]([OH:17])[CH:16]=[C:12]2[CH:11]=[N:10][N:9]=1.[I:18]Cl.O>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]2[N:14]=[C:15]([OH:17])[C:16]([I:18])=[C:12]2[CH:11]=[N:10][N:9]=1 | ClI | Oc1cc2cnnc(-c3ccccc3F)n2n1 | null | null | null | 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 | 25 | 1.25 | To a stirred mixture of 7-(2-fluorophenyl)pyrazolo[1,5-d][1,2,4]triazin-2-ol (0.5014 g, 2.18 mmol) in glacial acetic acid (10 ml) was added dropwise a 1.0 M solution of iodine monochloride in glacial acetic acid (3.26 ml, 3.26 mmol) and the mixture was stirred at room temperature for a total of 1.25 h. Water (40 ml) wa... | Oc1nn2c(-c3ccccc3F)nncc2c1I | null | 95 | null |
1,603,428 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH:19]=[O:20])=[CH:16][CH:17]=2)[C:12]([Br:21])=[N:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>CN(C=O)C>[Br:21][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=2)[N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[N:11]=1 | CC(C)(C)OC(=O)n1nc(Br)c2cc(C=O)ccc21 | null | null | Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 3 | Sodium borohydride (395 mg; 10.4 mmol; 2.9 eq.) was added in one portion to a solution of tert-butyl-3-bromo-5-formyl-1H-indazole-1-carboxylate (1.20 g; 3.58 mmol; 1.0 eq.) in DMF (30 mL). The reaction mixture was stirred for 3 h then poured into HCl (0.1N solution) and extracted with EtOAc. Combined organic phases wer... | CC(C)(C)OC(=O)n1nc(Br)c2cc(CO)ccc21 | null | 101.6 | null |
1,023,821 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | C(N(CC)CC)C.[NH2:8][C@@H:9]([CH2:12][CH3:13])[CH2:10][OH:11].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15].C(=O)([O-])O.[Na+]>O1CCCC1>[OH:11][CH2:10][C@@H:9]([NH:8][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N+:14]([O-:16])=[O:15])(=[O:24])=[O:25])[CH2:12][CH3... | O=[N+]([O-])c1ccccc1S(=O)(=O)Cl | CC[C@H](N)CO | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 0.17 | Triethylamine (0.94 ml, 6.74 mmol) was added to a solution of 400 mg (4.49 mmol) of (S)-2-aminobutan-1-ol in tetrahydrofuran (5 ml), and the mixture was stirred at room temperature for 10 min. 2-Nitrobenzenesulfonyl chloride (995.1 mg, 4.49 mmol) was added to the solution, and the mixture was stirred at room temperatur... | CC[C@@H](CO)NS(=O)(=O)c1ccccc1[N+](=O)[O-] | null | 99.1 | null |
250,629 | ord_dataset-41ea179beba54bed8cd874a5ec3469f7 | null | 1992-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3... | COC(=O)c1ccccc1Oc1ccc(C)cc1 | O=C1CCC(=O)N1Br | null | CC(C)(C#N)N=NC(C)(C)C#N | 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 | A solution of 35.08 g of methyl 2-(4-methylphenoxy)benzoate, 25.7 g of N-bromosuccinimide, 0.57 g of azobisisobutyronitrile, and 1200 mL of carbon tetrachloride was refluxed for 3 hours. After cooling to room temperature the resulting suspension was filtered and then concentrated in vacuo to provide 4.51 g of crude met... | COC(=O)c1ccccc1Oc1ccc(CBr)cc1 | null | 9.7 | null |
306,923 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | [CH:1]1([C:8]([CH2:10]Br)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:12]([C:15]1[CH:16]=[C:17](/[CH:21]=[CH:22]/[C:23](=[S:25])[NH2:24])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]>C(O)C>[CH:1]1([C:8]2[N:24]=[C:23](/[CH:22]=[CH:21]/[C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=3)[S:25][CH:10]... | NC(=S)/C=C/c1cccc([N+](=O)[O-])c1 | O=C(CBr)C1CCCCCC1 | 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 | 0 | null | A solution composed of 6.57 g of bromomethyl cycloheptyl ketone, 6.24 g of (E)-3-(3-nitrophenyl)-2-propenethioamide and 100 ml of ethyl alcohol was heated to reflux for 16 hr afterwhich it was diluted with 200 ml of ice water and extracted with methylene chloride. The combined extracts were washed with saturated sodium... | O=[N+]([O-])c1cccc(/C=C/c2nc(C3CCCCCC3)cs2)c1 | null | 62.7 | null |
113,279 | ord_dataset-f3b9c7d90d3648ff8136643f634ef2f0 | null | 1984-01-01T00:01:00 | true | [N+:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[C:6]([N+:12]([O-])=O)[C:5]=1[CH3:15])([O-])=O.N1CCOCC1>[Pt]>[NH2:1][C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[C:6]([NH2:12])[C:5]=1[CH3:15] | Cc1c([N+](=O)[O-])cc(Cl)c(Cl)c1[N+](=O)[O-] | null | null | [Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | The catalytic hydrogenation of 2,6-dinitro-3,4-dichlorotoluene with platinum at 45° C. under a hydrogen-pressure of 10 bar in the presence of catalytic amounts of morpholine gives, for example, the 2,6-diamino-3,4-dichlorotoluene in high yields and high purity. | Cc1c(N)cc(Cl)c(Cl)c1N | null | null | null |
62,977 | ord_dataset-9240b22758dd4f9e981f9ad2d5394155 | null | 1980-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.C([OH:18])(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N+:7]([O-:18])[CH:8]=[CH:9][CH:10]=1 | Clc1ccccc1Oc1cccnc1 | CC(C)O | 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 | null | A solution of 74.3 g of 3-(2-chlorophenoxy)pyridine [Agr. Biol. Ghem., 34, 68 (1970)] in 75 ml of glacial acetic acid in three equal portions. The temperature is maintained at 35°-40° C. for 16 hours and 75 ml of isopropanol is added and the mixture is refluxed 1 hour. The mixture is concentrated at reduced pressure an... | [O-][n+]1cccc(Oc2ccccc2Cl)c1 | null | null | null |
1,684,392 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][N:8]=2)[S:5][CH:6]=1>ClCCCl.O=[Mn]=O>[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][N:8]=2)[CH:13]=[O:14])[S:5][CH:6]=1 | Cc1csc(-c2cc(CO)ccn2)n1 | null | null | O=[Mn]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of (2-(4-methylthiazol-2-yl)pyridin-4-yl)methanol (750 mg; 3.64 mmol) in anh. DCE (40 ml) was treated with MnO2 (1.581 g; 18.20 mmol), and the resulting mixture was heated at reflux, under nitrogen, for 1.5 h. After cooling to rt, the resulting reaction mixture was filtered over celite, and the separated sol... | Cc1csc(-c2cc(C=O)ccn2)n1 | null | null | null |
1,663,056 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [F:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=O)=[C:4]([O:28][CH3:29])[CH:3]=1>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([O:28][CH3:29])[C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:13]=[C:14]([C... | COC(=O)c1ccc(C(=O)Nc2ccccc2Oc2ccc(F)cc2OC)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 130 | 8 | A stirring mixture of title compound 92 (2 g, 5.06 mmol) in polyphosphoric acid (4.76 ml, 41.7 mmol) was heated at 130° C. for 3 h. The reaction mixture was cooled, diluted with dichloromethane and water and stirred overnight. The layers were separated and the aqueous layer was extracted with dichloromethane. The combi... | COC(=O)c1ccc(C2=Nc3ccccc3Oc3c(OC)cc(F)cc32)cc1 | null | 6.5 | null |
1,548,771 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:9][CH:10]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[N:29]#[C:30]Br>C(Cl)(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[C... | CS(=O)(=O)c1ccc(OCC[C@@H]2C[C@@H]2C2CCNCC2)nc1 | N#CBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | 5-(Methylsulfonyl)-2-(2-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethoxy)pyridine (Step A, Example 11; 310 mg, 0.957 mmol) and potassium carbonate (489 mg, 3.54 mmol) were stirred in chloroform (15 mL). Cyanogen bromide (122 mg, 1.15 mmol) was added. The mixture was stirred at RT for 15 min and refluxed overnight. The mix... | CS(=O)(=O)c1ccc(OCC[C@@H]2C[C@@H]2C2CCN(C#N)CC2)nc1 | null | null | null |
159,436 | ord_dataset-41c90677d90b4fa5836ab66e2f5b4f51 | null | 1987-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][C:9](=[O:12])[CH:8]([C:13]([O:15][CH3:16])=[O:14])[S:7][C:6]=2[CH:17]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][C:9](=[O:12])[C:8]([CH2:19][CH2:20][CH2:21][Cl:22])([C:13]([O:15][CH3:16])=[O:14])[S:7][C:6]=2[CH:17]=1 | COC(=O)C1Sc2cc(Cl)ccc2OCC1=O | ClCCCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Methyl 7-chloro-3-oxo-3,4-dihydro-2H-1,5-benzoxathiepin-4-carboxylate is treated with 1-bromo-3-chloropropane in the same manner as described in Reference Example 25 to give methyl 7-chloro-4-(3-chloropropyl)-3-oxo-3,4-dihydro-2H-1,5-benzoxathiepin-4-carboxylate as a colorless oil. | COC(=O)C1(CCCCl)Sc2cc(Cl)ccc2OCC1=O | null | null | null |
212,024 | ord_dataset-e6e5ffd5405c481d8061087049155f9f | null | 1990-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:6]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=1)(=[O:7])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | O=C(Cl)c1ccc(Cl)nc1 | c1ccccc1 | null | [Al+3] | [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 | To 40 ml of a solution of 5.28 g of 6-chloronicotinoyl chloride in benzene, 16 g of aluminum chloride was added under ice-cooling and the resulting mixture was heated under reflux for six hours. After cooling, the reaction mixture was poured into a solution of ice/hydrochloric acid and extracted with ether. The organic... | O=C(c1ccccc1)c1ccc(Cl)nc1 | null | null | null |
1,332,948 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | C([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:23][CH2:22][N:21]([C:24](=[O:33])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=4[F:32])[CH2:20][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)(C)(C)C>C(O)=O>[Cl:31][C:27]1[C:26]([F:32])=[C:25]([CH:30]=[CH... | CCOC(=O)C1(Cc2cccc(Nc3ccnn3C(C)(C)C)n2)CCN(C(=O)c2cccc(Cl)c2F)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | 100 | 8 | 207 mg of ethyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-1-(3-chloro-2-fluorobenzoyl)piperidine-4-carboxylate was dissolved in 3 ml of formic acid at room temperature, followed by stirring the reaction mixture at 100° C. for 8 hours. The reaction mixture was cooled to room temperature, and concen... | CCOC(=O)C1(Cc2cccc(Nc3cc[nH]n3)n2)CCN(C(=O)c2cccc(Cl)c2F)CC1 | null | null | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.