Triethylamine → HCID 11606405, 화합물

HRID 969583노트

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HRID 969583 반응식
OC(C(F)(F)F)=O.[CH:8]([C@:11]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]1)([CH3:10])[CH3:9].[OH:33][C:34]1([C:41]2[S:42][C:43]([CH3:46])=[CH:44][N:45]=2)[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C([O-])(O)=O.[Na+]>[CH:8]([C@:11]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:29]([F:32])([F:30])[F:31])=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[CH2:15][CH2:14][C@@H:13]([NH:16][CH:37]2[CH2:38][CH2:39][C:34]([C:41]3[S:42][C:43]([CH3:46])=[CH:44][N:45]=3)([OH:33])[CH2:35][CH2:36]2)[CH2:12]1)([CH3:10])[CH3:9]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 590174344-Hydroxy-4-(5-methyl-thiazol-2-yl)-cyclohexanoneHCID 86601913HCID 86601913, 화합물

생성물 1

HCID 11606405HCID 11606405, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of (1R,3S)-3-isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentanamine TFA salt (40 mg, 0.1 mmol) of Step C-2 from Example 1 and 4-hydroxy-4-(5-methyl-1,3-thiazol-2-yl)cyclohexanone (32.6 mg, 0.15 mmol) in dichloromethane (10 mL) was added triethylamine (31 μL, 0.22 mmol) followed by sodium triacetoxyborohydride (56 mg, 0.26 mmol) at room temperature. After being stirred overnight, the mixture was diluted with methylene chloride and neutralized with NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica eluting with 5% MeOH/CH2Cl2 to give two isomers (13 mg and 10 mg). LC-MS calculated for C29H38F3N3O2S: (M+H)+550; found 550.2.

후처리

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica eluting with 5% MeOH/CH2Cl2
  4. customto give two isomers (13 mg and 10 mg)

출처 및 근거

ORD 기록
ord-b8a18d708d0248d6bc2e8ee6b7015cac
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307086B2

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