Tetrahydrofuran → HCID 118061901, 화합물

HRID 920809노트

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HRID 920809 반응식
[F:1][C:2]1([F:10])[CH2:6][CH2:5][CH:4](C(O)=O)[CH2:3]1.C1C=CC(P([N:25]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[C:44]([C:45]([NH2:47])=[O:46])=[C:39]3[CH2:40][NH:41][CH2:42][CH2:43][N:38]3[N:37]=2)[CH:32]=[CH:33][C:34]=1[F:35].C1[CH2:52][O:51]CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[C:44]([C:45]([NH2:47])=[O:46])=[C:39]3[CH2:40][N:41]([C:52]([NH:25][CH:4]4[CH2:5][CH2:6][C:2]([F:1])([F:10])[CH2:3]4)=[O:51])[CH2:42][CH2:43][N:38]3[N:37]=2)[CH:32]=[CH:33][C:34]=1[F:35]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 199401P,P-Diphenylphosphinic azideHCID 534038373,3-Difluorocyclopentane-1-carboxylic acidHCID 1180616272-(3-Chloro-4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-3-carboxamide

생성물 1

HCID 118061901HCID 118061901, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

A stirred solution of Intermediate 332C (32.6 mg, 0.217 mmol) in toluene (1 mL) at RT under nitrogen was added with TEA (0.045 mL, 0.325 mmol) and DPPA (0.050 mL, 0.217 mmol) and heated to 70° C. for 2 h. The reaction mass was cooled to RT and to it was added a solution of Intermediate 185B (30 mg, 0.108 mmol) in THF (1 mL) and stirred at RT for 16 h. The reaction mass was diluted with ethyl acetate (25 mL), washed with water and brine, dried over anhydrous Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The individual isomers were separated by preparative chiral SFC (Column: WHELK-O® 1 (R,R) (250×4.6 mm), 5μ column, 5 Co-Solvent: 0.2% DEA, Column Temperature: 24.4, Total Flow: 3 mL, CO2 Flow Rate: 2.1, Co-Solvent Flow Rate: 0.9, Co-Solvent %: 30%, Back Pressure: 101 bar.

후처리

  1. temperatureThe reaction mass was cooled to RT and to it
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe individual isomers were separated by preparative chiral SFC (Column

출처 및 근거

ORD 기록
ord-14f80af829e246b6a911eefc35597fd8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273058B2

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