Trifluoroacetic acid → 1-(2-(2-(2-((1-(Azetidin-3-yl)-1H-pyrazol-4-yl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592388노트

반응식

HRID 592388 반응식
C(O)(C(F)(F)F)=O.[C:8]([C:11]1([C:14]2[CH:45]=[CH:44][CH:43]=[CH:42][C:15]=2[CH2:16][CH2:17][C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]3[CH:27]=[N:28][N:29]([CH:31]4[CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]4)[CH:30]=3)[N:19]=2)[CH2:13][CH2:12]1)(=[O:10])[NH2:9]>C(Cl)Cl>[NH:33]1[CH2:32][CH:31]([N:29]2[CH:30]=[C:26]([NH:25][C:20]3[N:19]=[C:18]([CH2:17][CH2:16][C:15]4[CH:42]=[CH:43][CH:44]=[CH:45][C:14]=4[C:11]4([C:8]([NH2:9])=[O:10])[CH2:12][CH2:13]4)[C:23]([Cl:24])=[CH:22][N:21]=3)[CH:27]=[N:28]2)[CH2:34]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86712299tert-Butyl 3-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate

생성물 1

HCID 732965761-(2-(2-(2-((1-(Azetidin-3-yl)-1H-pyrazol-4-yl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (1 mL) was added to a solution of tert-butyl 3-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate A18 (0.110 g, 0.204 mmol) in DCM (5 mL) and the reaction was stirred for 16 hours. The volatiles were removed in vacuo and the resultant residue loaded onto an SCX cartridge (5 g). The cartridge was washed with MeOH (100 mL) and then with 5% NH4OH in MeOH (100 mL). The basic fractions were combined and the solvent was removed in vacuo to give the title compound 14 as a tan solid (61 mg, 68%). 1H NMR (400 MHz, d4-MeOD) δ 8.27 (s, 1H), 8.09 (s, 1H), 7.65 (s, 1H), 7.44-7.37 (m, 2H), 7.34 (m, 1H), 7.27 (m, 1H), 5.36-5.18 (m, 1H), 4.15 (m, 2H), 3.96 (m, 2H), 3.20 (m, 4H), 1.63 (m, 2H), 1.20-1.05 (m, 2H). LCMS-C: rt 4.30 min; m/z 438.0 [M+H]+.

후처리

  1. customThe volatiles were removed in vacuo
  2. washThe cartridge was washed with MeOH (100 mL)
  3. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-1457b703f6c94a3f848df8e8c11966a7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238644B2

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