Triethylamine → HCID 11606405, compound

HRID 969583Notes

Reaction equation

HRID 969583 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 11606405HCID 11606405, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b8a18d708d0248d6bc2e8ee6b7015cac
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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