Trifluoroacetic acid → HCID 86679746, 화합물

HRID 77459노트

반응식

HRID 77459 반응식
[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]

참가 물질

4

반응물 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

생성물 1

HCID 86679746HCID 86679746, 화합물수율 61.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-69b1659f855f4a008f262ea7106ad62e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841301B2

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