Heptane → 2-chloro-3-(1-cyano-1-methylethoxy)-N-{5-[{2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}(methyl)amino]-2-fluorophenyl}benzamide ethanedioate

HRID 1800641Notes

Reaction equation

HRID 1800641 reaction equation
[Cl:1][C:2]1[C:34]([O:35][C:36]([C:39]#[N:40])([CH3:38])[CH3:37])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([N:13]([C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH3:14])[CH:10]=[CH:9][C:8]=1[F:30])=[O:5].O.O.[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45].CCCCCCC>C(OCC)(=O)C>[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45].[Cl:1][C:2]1[C:34]([O:35][C:36]([C:39]#[N:40])([CH3:38])[CH3:37])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([N:13]([C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH3:14])[CH:10]=[CH:9][C:8]=1[F:30])=[O:5]

Participants

5

Reactant 3

HCID 8900HeptaneHCID 61373Oxalic acid dihydrateHCID 252063462-Chloro-3-[(2-Cyanopropan-2-Yl)oxy]-N-{5-[{2-[(Cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-B]pyridin-5-Yl}(Methyl)amino]-2-Fluorophenyl}benzamide

Product 1

HCID 866460602-chloro-3-(1-cyano-1-methylethoxy)-N-{5-[{2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}(methyl)amino]-2-fluorophenyl}benzamide ethanedioateYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-3-(1-cyano-1-methylethoxy)-N-{5-[{2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}(methyl)amino]-2-fluorophenyl}benzamide (300 mg, 0.518 mmol) produced in Example C122(xi) was dissolved in ethyl acetate (9 mL), oxalic acid dihydrate (68.6 mg, 0.544 mmol) was added, and the mixture was stood at 55° C. To the obtained solution was added heptane, and the mixture was cooled to room temperature. The crystallized crystals were collected by filtration, and dried to give the title compound (339 mg, 98%) as colorless crystals.

Workup

  1. customwas stood at 55° C
  2. filtrationThe crystallized crystals were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-1ffbec1a67be4f6da5eabc410aa509eb
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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