Trifluoroacetic acid → HCID 86679746、化合物

HRID 77459ノート

反応式

HRID 77459 の反応式
[F:1][C:2]([F:38])([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:36]=[CH:35][C:22]4[N:23]([CH2:27][O:28]CC[Si](C)(C)C)[C:24](=[O:26])[O:25][C:21]=4[CH:20]=3)=[CH:13][N:12]=2)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:28][CH2:27][N:23]1[C:22]2[CH:35]=[CH:36][C:19]([O:18][CH2:17][C:14]3[CH:13]=[N:12][C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:38])([F:1])[F:37])=[CH:5][CH:6]=4)=[N:16][CH:15]=3)=[CH:20][C:21]=2[O:25][C:24]1=[O:26]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 866797456-((2-((4-(trifluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]oxazol-2(3H)-one

生成物 1

HCID 86679746HCID 86679746、化合物収率 61.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 6-((2-((4-(trifluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]oxazol-2(3H)-one (0.05 g, 0.091 mmol) in DCM (3 mL) at 0° C., TFA (0.035 mL, 0.456 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. Solvent was removed under vacuum and the residue was washed with diethyl ether. The crude product was purified by preparative HPLC on an Inertsil ODS column (19×250 mm, 5μ) using 0 to 65% mobile phase B (ACN) in mobile phase A (0.1% TFA) over 6 min to give 3-(hydroxymethyl)-6-((2-((4-(trifluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)benzo[d]oxazol-2(3H)-one as a white solid (0.025 g, 61%). 1H-NMR: 400 MHz, DMSO-d6 δ ppm 5.03 (s, 2H), 5.19 (s, 2H), 6.92-6.95 (m, 1H), 7.21-7.32 (m, 4H), 7.86-7.88 (m, 1H), 8.62 (s, 2H), 9.96 (s, 1H). LCMS: R.T. 2.303 min; 449 [M+H]+.

後処理

  1. customSolvent was removed under vacuum
  2. washthe residue was washed with diethyl ether
  3. customThe crude product was purified by preparative HPLC on an Inertsil ODS column (19×250 mm, 5μ)
  4. customover 6 min

出典と根拠

ORDレコード
ord-69b1659f855f4a008f262ea7106ad62e
出典データセット
uspto-grants-2014_09
特許番号
US08841301B2

反応ノート

読み込み中…