Lithium Hydroxide → HCID 178489079, 화합물

HRID 2173950노트

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HRID 2173950 반응식
[C:1]([C:3]1[CH:36]=[CH:35][C:6]2[NH:7][C:8]([C:10]([C:23]3[C:31]([O:32][CH3:33])=[CH:30][C:29]([CH3:34])=[C:28]4[C:24]=3[CH:25]=[CH:26][NH:27]4)([O:15][CH:16]([F:22])[C:17]([O:19]CC)=[O:18])[C:11]([F:14])([F:13])[F:12])=[N:9][C:5]=2[CH:4]=1)#[N:2].[Li+].[OH-]>C1COCC1.O.CO>[C:1]([C:3]1[CH:36]=[CH:35][C:6]2[NH:7][C:8]([C:10]([C:23]3[C:31]([O:32][CH3:33])=[CH:30][C:29]([CH3:34])=[C:28]4[C:24]=3[CH:25]=[CH:26][NH:27]4)([O:15][CH:16]([F:22])[C:17]([OH:19])=[O:18])[C:11]([F:12])([F:13])[F:14])=[N:9][C:5]=2[CH:4]=1)#[N:2]

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 178472324HCID 178472324, 화합물

생성물 1

HCID 178489079HCID 178489079, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (±)-ethyl 2-(1-(5-cyano-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethoxy)-2-fluoroacetate (Example 35-F) (60 mg, 0.119 mmol) in THF (1.0 mL), water (1.0 mL) and MeOH (0.20 mL) was added LiOH (25 mg, 0.595 mmol) and this mixture was stirred for 16 hr at room temperature. The reaction was partitioned between EtOAc and cold 1N HCl solution and the layers separated and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. This material was purified with FCC eluting with dichloromethane/MeOH (0-10%) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.03 (br.s., 1H) 10.96 (br.s, 1H), 8.17-8.34 (br.s., 1H) 7.78-7.97 (br.s., 1H) 7.53-7.59 (m, 1H) 7.19-7.29 (m, 1H) 7.00-7.02 (br.s, 1H) 6.74-6.79 (br.s., 1H), 6.65 (s., 1H), 4.87-5.37 (m, 1H) 3.01 (s, 3H) 2.46 (s, 3H). HRMS calcd. for C22H16F4N4O4 (M+H)+ 477.1141. found 477.1154.

후처리

  1. customThe reaction was partitioned between EtOAc and cold 1N HCl solution
  2. customthe layers separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis material was purified with FCC
  8. washeluting with dichloromethane/MeOH (0-10%)

출처 및 근거

ORD 기록
ord-87268fa544b14892b8b27c56ef22ed34
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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