Acetic Acid → HCID 57438764, compound

HRID 2233092Notes

Reaction equation

HRID 2233092 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[N:15]4[CH:16]=[CH:17][N:18]=[C:19]([O:20]C)[C:14]4=[N:13][C:12]=3[C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.Br.C(O)(=O)C>CCOCC>[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[N:15]4[CH:16]=[CH:17][NH:18][C:19](=[O:20])[C:14]4=[N:13][C:12]=3[C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 57438765HCID 57438765, compound

Product 1

HCID 57438764HCID 57438764, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclopropyl-{4-[2-(4-fluorophenyl)-8-methoxyimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-amine (Example #A.10.1, 0.156 g, 0.414 mmol) was treated with a 4 M solution of hydrogen bromide in acetic acid (3 mL, 12 mmol) at ambient temperature. After about 45 min the mixture was treated with Et2O and filtered, washing the solid successively with Et2O, saturated aqueous NaHCO3 and Et2O. The solid was then dried in the oven for about 16 h to yield the product as white solid (0.115 g, 77%): LC/MS (Table 1, Method b) Rt=1.7 min; MS m/z: 361.4 (M−H)−.

Workup

  1. filtrationfiltered
  2. washwashing the solid successively with Et2O, saturated aqueous NaHCO3 and Et2O
  3. customThe solid was then dried in the oven for about 16 h

Sources & evidence

ORD record
ord-8c3daf0de1e84f2f8274ae34120e53f9
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

Loading…