Diisopropylethylamine → HCID 67362734, compound

HRID 245723Notes

Reaction equation

HRID 245723 reaction equation
Cl.[Br:2][C:3]1[N:4]=[C:5]([C@@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[N:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[C:7]=12.Cl.[Br:19][C:20]1[N:21]=[C:22]([C@H:30]2[CH2:34][CH2:33][NH:32][CH2:31]2)[N:23]2[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[C:24]=12.C(N(CC)C(C)C)(C)C.[CH3:44][O:45][CH2:46][C:47]([Cl:49])=[O:48]>ClCCl>[ClH:49].[Br:2][C:3]1[N:4]=[C:5]([C@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[N:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[C:7]=12.[Br:19][C:20]1[N:21]=[C:22]([C@H:30]2[CH2:34][CH2:33][N:32]([C:47](=[O:48])[CH2:46][O:45][CH3:44])[CH2:31]2)[N:23]2[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[C:24]=12

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 67363157HCID 67363157, compoundHCID 67365099HCID 67365099, compound

Product 2

HCID 67362734HCID 67362734, compoundHCID 67363157HCID 67363157, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(S)-1-Bromo-8-methyl-3-(pyrrolidin-3-yl)imidazo[1,5-a]pyrazine hydrochloride was prepared in a similar way as (R)-1-bromo-8-methyl-3-(pyrrolidin-3-yl)imidazo[1,5-a]pyrazine hydrochloride. To (S)-1-bromo-8-methyl-3-(pyrrolidin-3-yl)imidazo[1,5-a]pyrazine hydrochloride (0.31 mmol, 100 mg) in dichloromethane (5 ml) and N,N-diisopropylethylamine (1.778 mmol, 0.311 ml) at 0° C. was added a solution of methoxyacetyl chloride (0.534 mmol, 0.049 ml) in dichloromethane (0.5 ml). After stirring for one hour at room temperature the reaction mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogencarbonate solution, water, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give (S)-1-(3-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidin-1-yl)-2-methoxyethanone (80 mg).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution, water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol)

Sources & evidence

ORD record
ord-61075b0c0f0f4ee1add06b0905350984
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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