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

HRID 1800649노트

반응식

HRID 1800649 반응식
[Cl:1][C:2]1[C:10]([O:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:17][C:18]1[CH:19]=[C:20]([NH:25][C:26]2[N:31]=[C:30]3[S:32][C:33]([NH:35][C:36]([CH:38]4[CH2:40][CH2:39]4)=[O:37])=[N:34][C:29]3=[CH:28][CH:27]=2)[CH:21]=[CH:22][C:23]=1[F:24].C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[Cl:1][C:2]1[C:10]([O:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:17][C:18]1[CH:19]=[C:20]([NH:25][C:26]2[N:31]=[C:30]3[S:32][C:33]([NH:35][C:36]([CH:38]4[CH2:40][CH2:39]4)=[O:37])=[N:34][C:29]3=[CH:28][CH:27]=2)[CH:21]=[CH:22][C:23]=1[F:24])=[O:5]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 86646062N-{5-[(3-amino-4-fluorophenyl)amino][1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamideHCID 866460652-Chloro-3-(1-cyano-1-methylethoxy)benzoyl chloride

생성물 1

HCID 252063492-chloro-3-(1-cyano-1-methylethoxy)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}amino)-2-fluorophenyl]benzamide수율 66%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 2-chloro-3-(1-cyano-1-methylethoxy)benzoyl chloride synthesized above in N,N-dimethylacetamide (4.0 mL) was added N-{5-[(3-amino-4-fluorophenyl)amino][1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide (200 mg, 0.582 mmol), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (20 mL), and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with water (20 mL) and saturated brine (20 mL), and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100) and crystallized from hexane/ethyl acetate to give the title compound (216 mg, 66%) as pale-purple crystals.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with water (20 mL) and saturated brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100)
  6. customcrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-bb5c7da81829443baf0b5181ed221a3f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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