Triethylamine → 4-[((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)amino]-1-(1,3-oxazol-2-yl)cyclohexanol

HRID 969565ノート

反応式

HRID 969565 の反応式
[CH:1]([C@:4]1([C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]([F:25])([F:24])[F:23])=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])[CH2:8][CH2:7][C@@H:6]([NH2:9])[CH2:5]1)([CH3:3])[CH3:2].[OH:26][C:27]1([C:34]2[O:35][CH:36]=[CH:37][N:38]=2)[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH:1]([C@:4]1([C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]([F:25])([F:23])[F:24])=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:30]2[CH2:31][CH2:32][C:27]([C:34]3[O:35][CH:36]=[CH:37][N:38]=3)([OH:26])[CH2:28][CH2:29]2)[CH2:5]1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58784490((1S,3R)-3-amino-1-isopropylcyclopentyl)(7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanoneHCID 590174384-Hydroxy-4-oxazol-2-yl-cyclohexanone

生成物 1

HCID 115916914-[((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)amino]-1-(1,3-oxazol-2-yl)cyclohexanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran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 (113.0 mg, 0.3188 mmol) of Step C-2 of Example 1 in THF (1 mL) was added 4-hydroxy-4-(1,3-oxazol-2-yl)cyclohexanone (80.3 mg, 0.443 mmol) followed by triethylamine (0.5 mL, 3.6 mmol) and finally sodium triacetoxyborohydride (135 mg, 0.638 mmol). After being stirred overnight, the reaction was quenched by addition of NaOH solution. The resulting solution was extracted with methylene chloride. The extract was dried over MgSO4 and evaporated in vacuo. The residue was purified by flash chromatography eluting with EtOAc/1% NH4OH to give two isomers. Isomer 1: 73 mg. MS calculated for C28H36F3N3O3: (M+H)+520; found 520.1. Isomer 2: 56 mg. MS found 520.1.\

後処理

  1. customthe reaction was quenched by addition of NaOH solution
  2. extractionThe resulting solution was extracted with methylene chloride
  3. dry with materialThe extract was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with EtOAc/1% NH4OH
  7. customto give two isomers

出典と根拠

ORDレコード
ord-a53bddcdee0642568f4b8955a5262740
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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