Butanoic acid, 4-chloro-4-oxo-, methyl ester → Methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoate

HRID 1177634

반응식

HRID 1177634 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH2:26])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.C(N(C(C)C)C(C)C)C.Cl[C:37](=[O:44])[CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41]>C1COCC1.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:26][C:37](=[O:44])[CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2

참가 물질

6

반응물 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 81531DiisopropylethylamineHCID 574030523-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine

생성물 1

HCID 67111772Methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine (140 mg, 0.387 mmol) was dissolved in THF (3.9 mL) and N-ethyl-N-isopropylpropan-2-amine (270 μl, 1.55 mmol) before methyl 4-chloro-4-oxobutanoate (189 μl, 1.55 mmol) was added at ambient temperature and the reaction mixture was stirred at ambient temperature for 30 min. The reaction mixture was diluted with 100 mL of DCM, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoate after flash chromatography. MS (ESI) m/z: Calculated: 475.1; Observed: 476.4 (M++1).

후처리

  1. additionadded to a separatory funnel
  2. custompartitioned with water
  3. washwashed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap

출처 및 근거

ORD 기록
ord-195398b5271f421c8d816273a66dd89a
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

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