Acetic Acid → HCID 66738579、化合物

HRID 2047208ノート

反応式

HRID 2047208 の反応式
[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]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 667335321251772-69-6HCID 86664791HCID 86664791、化合物

生成物 1

HCID 66738579HCID 66738579、化合物収率 30%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-7f0159e39aae4f298948814ab096e6f9
出典データセット
uspto-grants-2013_11
特許番号
US08591943B2

反応ノート

読み込み中…