Methylamine → HCID 66734210, compound

HRID 1929719Notes

Reaction equation

HRID 1929719 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:20][CH3:21])=[N:15][C:16]([C:17](O)=[O:18])=[C:10]2[CH:9]1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][N:35](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CN.C1COCC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:20][CH3:21])=[N:15][C:16]([C:17](=[O:18])[NH:35][CH3:34])=[C:10]2[CH:9]1[CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66734099HCID 66734099, compound

Product 1

HCID 66734210HCID 66734210, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylic acid 7-tert-butyl ester (47 mg; 0.100 mmol) in anhydrous DMF (1 ml) was added successively TBTU (35 mg; 0.110 mmol), DIPEA (51 μl; 0.300 mmol), and finally 2M methylamine in THF (0.15 ml; 0.300 mmol). The resulting reaction mixture was further stirred at rt, under nitrogen, for 16 h, and was then purified by preparative HPLC to give the pure product 3-ethyl-1-methylcarbamoyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (27.8 mg; 0.057 mmol; 58%).

Workup

  1. customThe resulting reaction mixture
  2. customwas then purified by preparative HPLC

Sources & evidence

ORD record
ord-ca13e2349c604e0199d2b594579096e6
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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