Acetic Acid → HCID 66738579, 화합물

HRID 2047208노트

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HRID 2047208 반응식
[CH3:1][C@@H:2]1[CH2:7][CH:6]([NH2:8])[CH2:5][C@H:4]([CH3:9])[O:3]1.[CH3:10][Si:11]([CH3:49])([CH3:48])[CH2:12][CH2:13][O:14][CH2:15][N:16]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:17]1[N:22]2[N:23]=[CH:24][C:25]([C:26]3[CH:27]=[N:28][C:29]4[C:34]([CH:35]=3)=[CH:33][C:32]([F:36])=[CH:31][CH:30]=4)=[C:21]2[N:20]=[C:19]([CH:37]=O)[C:18]=1[Br:39].CC(O)=O.[BH3-]C#N.[Na+]>ClCCCl.C(O)C.C(Cl)Cl>[Br:39][C:18]1[C:19]([CH2:37][NH:8][CH:6]2[CH2:5][C@H:4]([CH3:9])[O:3][C@H:2]([CH3:1])[CH2:7]2)=[N:20][C:21]2[N:22]([N:23]=[CH:24][C:25]=2[C:26]2[CH:27]=[N:28][C:29]3[C:34]([CH:35]=2)=[CH:33][C:32]([F:36])=[CH:31][CH:30]=3)[C:17]=1[N:16]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:46])[CH3:47])[CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:48])([CH3:49])[CH3:10]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 667335321251772-69-6HCID 86664791HCID 86664791, 화합물

생성물 1

HCID 66738579HCID 66738579, 화합물수율 30%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

To crude (2R,6S)-2,6-dimethyltetrahydro-2H-pyran-4-amine (0.18 g) in DCE (4.2 ml) and Ethanol (4.2 ml) was added 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde (0.19 g, 0.3 mmol) followed by AcOH (0.03 ml, 0.6 mmol). After stirring for 30 minutes at room temperature, NaBH3CN (37.8 mg, 0.6 mmol) was added and stirring was continued further for 30 minutes more. LC/MS showed no starting material remaining. After the solvent was rotoevaporated, the crude was dissolved with DCM (20 ml), washed with sat. NaHCO3 (1×5 ml), water (1×5 ml), brine (1×5 ml), dried over MgSO4. Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with EtOAc/Hexanes (0-60%) gave desired 6-bromo-5-(((2R,6S)-2,6-dimethyltetrahydro-2H-pyran-4-ylamino)methyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (68 mg, 30%).

후처리

  1. stirringstirring
  2. waitwas continued further for 30 minutes
  3. washwashed with sat. NaHCO3 (1×5 ml), water (1×5 ml), brine (1×5 ml)
  4. dry with materialdried over MgSO4
  5. customSolvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel
  7. washElution with EtOAc/Hexanes (0-60%)

출처 및 근거

ORD 기록
ord-7f0159e39aae4f298948814ab096e6f9
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591943B2

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