Sodium triacetoxyborohydride → HCID 11364827, compound

HRID 2367009Notes

Reaction equation

HRID 2367009 reaction equation
[OH:1][C:2]1([C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:15][CH3:16])=[O:14])=[CH:11][N:10]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH2:19][C@H:20]1[CH2:24][CH2:23][N:22]([C:25](=[O:40])[CH2:26][NH:27][C:28](=[O:39])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:1][C:2]1([C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:15][CH3:16])=[O:14])=[CH:11][N:10]=2)[CH2:7][CH2:6][CH:5]([NH:19][C@H:20]2[CH2:24][CH2:23][N:22]([C:25](=[O:40])[CH2:26][NH:27][C:28](=[O:39])[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:38])[F:36])[CH:30]=3)[CH2:21]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 57803303HCID 57803303, compoundHCID 57803383HCID 57803383, compound

Product 1

HCID 11364827HCID 11364827, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(1-Hydroxy-4-oxocyclohexyl)-N-methylnicotinamide (100 mg, 0.4 mmol) and 126 mg (0.4 mmol) of N-{2-[(3S)-3-aminopyrrolidin-1-yl]-2-oxoethyl}-3-(trifluoromethyl)benzamide were dissolved in 10.0 mL of methylene chloride. To the solution was added 170 mg (0.8 mmol) of sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 2 h. Direct chromatography on silica gel gave 48 mg (23%) of the final desired product (top spot on TLC and first peak on HPLC). MS: (M+H)+ 547.

Sources & evidence

ORD record
ord-648aecc5bbd346218248568c225671dc
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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