Triethylamine → 1-(methoxy-methyl-carbamoyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester

HRID 221480Notes

Reaction equation

HRID 221480 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:20]([F:23])([F:22])[F:21])=[N:15][C:16]([C:17]([OH:19])=O)=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[CH2:26][NH2:27].C(N(CC)CC)C.[O:35]=[C:36]1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:20]([F:21])([F:23])[F:22])=[N:15][C:16]([C:17](=[O:19])[N:27]([O:35][CH3:36])[CH3:26])=[C:10]2[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 177781771-MethoxymethanamineHCID 575184537-[(tert-Butoxy)carbonyl]-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylic acid

Product 1

HCID 575184541-(methoxy-methyl-carbamoyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl esterYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylic acid 7-tert-butyl ester 27d (1.84 g, 5.5 mmol) and N-methoxy methyl-amine (0.805 g, 8.25 mmol) were dissolved in 50 mL of dichloromethane under stirring, and triethylamine (3 mL, 22 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (2.1 g, 8.25 mmol) were then added to the solution. The reaction mixture was reacted overnight at room temperature and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 1-(methoxy-methyl-carbamoyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester 27e (2.1 g) as a white solid.

Workup

  1. customThe reaction mixture was reacted overnight at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf13463230724e0a99a3b4dd52dbdf79
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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