Trifluoroacetic acid → HCID 71143541, 화합물

HRID 2363274노트

반응식

HRID 2363274 반응식
[C:1]([CH2:3][C:4]1([N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]4[N:31](COCC[Si](C)(C)C)[CH:32]=[CH:33][C:26]=34)[CH:22]=[N:21]2)[CH2:7][N:6]([C:8]2[CH:19]=[CH:18][C:11]([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:5]1)#[N:2].FC(F)(F)C(O)=O>>[C:1]([CH2:3][C:4]1([N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]4[NH:31][CH:32]=[CH:33][C:26]=34)[CH:22]=[N:21]2)[CH2:5][N:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:18][CH:19]=2)[CH2:7]1)#[N:2]

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 71143552HCID 71143552, 화합물

생성물 1

HCID 71143541HCID 71143541, 화합물

실험 절차

4-{3-(Cyanomethyl)-3-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-isopropylbenzamide was dissolved in dichloromethylene (5 mL). To the solution was added trifluoroacetic acid (TFA) (2.5 mL). The mixture was stirred at room temperature for 1 hour. The volatiles were removed under reduced pressure. The residue was dissolved in methanol (10 mL). To the solution was added ethylenediamine (1 mL). The mixture was stirred at room temperature for 4 hours, and was purified by RP-HPLC (pH=10) to afford the desired product (0.415 g). LCMS (M+H)+: m/z=440.1. The high purity (99.6%) of the product was obtained by re-crystallization from acetone-ether, 1H NMR (400 MHz, CDCl3): δ 9.57 (s, 1H), 8.31 (d, J=4.9 Hz, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.70 (m, 2H), 7.39 (d, J=3.4 Hz, 1H), 7.18 (d, J=4.9 Hz, 1H), 6.70 (d, J=3.4 Hz, 1H), 6.55 (m, 2H), 5.79 (d, J=7.8 Hz, 1H), 4.47 (d, J=8.3 Hz, 2H), 4.38 (d, J=8.3 Hz, 2H), 4.27 (m, 1H), 3.45 (s, 2H), 1.25 (d, J=6.7 Hz, 6H).

후처리

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (10 mL)
  3. additionTo the solution was added ethylenediamine (1 mL)
  4. stirringThe mixture was stirred at room temperature for 4 hours
  5. customwas purified by RP-HPLC (pH=10)

출처 및 근거

ORD 기록
ord-0e36013e2abc4fd790ee6536b425ea38
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691807B2

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