Triethylamine → HCID 11606405、化合物

HRID 969583ノート

反応式

HRID 969583 の反応式
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]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 590174344-Hydroxy-4-(5-methyl-thiazol-2-yl)-cyclohexanoneHCID 86601913HCID 86601913、化合物

生成物 1

HCID 11606405HCID 11606405、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b8a18d708d0248d6bc2e8ee6b7015cac
出典データセット
uspto-grants-2007_12
特許番号
US07307086B2

反応ノート

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