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

HRID 592388
ノート
印刷プレビュー

反応式

HRID 592388 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-1457b703f6c94a3f848df8e8c11966a7
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238644B2

反応ノート

読み込み中…

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