Water → HCID 178495935, compound

HRID 245698Notes

Reaction equation

HRID 245698 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.C(N(CC)CC)C.[C:30](Cl)(=[O:32])[CH3:31].O>ClCCl>[Br:1][C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]([CH2:19][CH2:20][O:21][CH3:22])[C:30](=[O:32])[CH3:31])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178495950HCID 178495950, compound

Product 1

HCID 178495935HCID 178495935, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)-N-(2-methoxyethyl)cyclohexanamine (0.182 mmol, 67 mg) in dichloromethane (2 ml) and triethylamine (0.912 mmol, 0.127 ml) at 0° C. was added acetyl chloride (0.274 mmol, 0.020 ml). After stirring for 1 hour dichloromethane and water were added. The organic layer was separated, dried over a phase separation filter and concentrated in vacuo to give N-((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)-N-(2-methoxyethyl)acetamide (72 mg).

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. customdried over a phase separation
  4. filtrationfilter
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe06679c5efe48b286428be0b375431d
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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