Acetonitrile → Cyclopropanecarboxamide, N-((4-((8-chloro-4,10-dihydro-1-methylpyrazolo(3,4-b)(1,5)benzodiazepin-5(1H)-yl)carbonyl)-2-fluorophenyl)methyl)-, 4-methylbenzenesulfonate

HRID 1521461Notes

Reaction equation

HRID 1521461 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:26]([C:27]([C:29]3[CH:41]=[CH:40][C:32]([CH2:33][NH:34][C:35]([CH:37]4[CH2:39][CH2:38]4)=[O:36])=[C:31]([F:42])[CH:30]=3)=[O:28])[CH2:25][C:24]3[CH:23]=[N:22][N:21]([CH3:43])[C:20]=3[NH:19][C:18]=2[CH:44]=1.C(#N)C.C(OCC)(=O)C>C(O)C(C)C.C1(C)C=CC=CC=1.C(O)C(C)C>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:26]([C:27]([C:29]3[CH:41]=[CH:40][C:32]([CH2:33][NH:34][C:35]([CH:37]4[CH2:38][CH2:39]4)=[O:36])=[C:31]([F:42])[CH:30]=3)=[O:28])[CH2:25][C:24]3[CH:23]=[N:22][N:21]([CH3:43])[C:20]=3[NH:19][C:18]=2[CH:44]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 135564707VA-111913

Product 1

HCID 135565015Cyclopropanecarboxamide, N-((4-((8-chloro-4,10-dihydro-1-methylpyrazolo(3,4-b)(1,5)benzodiazepin-5(1H)-yl)carbonyl)-2-fluorophenyl)methyl)-, 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 6560IsobutanolSolventHCID 66787386Toluene iso-butanolSolvent

Procedure

A solution of para-toluenesulfonic acid monohydrate in iso-butanol was added to a solution of cyclopropanecarboxylic acid 4-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraazabenzo[f]azulene-9-carbonyl)-2-fluoro-benzylamide in toluene/iso-butanol. Acetonitrile and ethyl acetate were added. The solution was allowed to cool and seeded with crystals of the title compound (as prepared herein above). After further cooling and stirring, the product was isolated by filtration, washed with ethyl acetate and then dried.

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-ed5fde46edf04fd1932b7de1cb17a256
Source dataset
uspto-grants-2015_07
Patent number
US09073928B2

Reaction notes

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