Triethylamine → HCID 11692307, compound

HRID 969586Notes

Reaction equation

HRID 969586 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:45][CH:44]=[N:43][CH:42]=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[CH2:36][CH2:35][C:34]([C:41]3[S:45][CH:44]=[N:43][CH:42]=3)([OH:33])[CH2:39][CH2:38]2)[CH2:12]1)([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 590174394-Hydroxy-4-(thiazol-5-yl)cyclohexanoneHCID 86601913HCID 86601913, compound

Product 1

HCID 11692307HCID 11692307, 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 (30.0 mg, 0.0846 mmol) from Step C-2 of Example 1 and 4-hydroxy-4-(1,3-thiazol-5-yl)cyclohexanone (23.4 mg, 0.119 mmol) in dichloromethane (8 mL) was added triethylamine (0.0236 mL, 0.169 mmol) followed by sodium triacetoxyborohydride (42 mg, 0.20 mmol) at room temperature. After being stirred overnight, the mixture was diluted with dichloromethane and neutralized with saturated NaHCO3. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give two isomers. LC-MS for both isomers: calculated for C28H36F3N3O2S (M+H)+536; found 536.2.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with 5% MeOH/CH2Cl2
  5. customto give two isomers

Sources & evidence

ORD record
ord-a8c1d8ad7f9d455faa6f315c15e3b347
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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