Formic Acid → HCID 178508478, compound

HRID 449053Notes

Reaction equation

HRID 449053 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([NH2:20])[C:14]3=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].C(O)=O>CCO.O>[NH2:20][C:19]1[C:14]2[N:15]([C:11]([C@H:8]3[CH2:7][CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]3)=[N:12][C:13]=2[C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:25][CH:26]=2)[CH:16]=[CH:17][N:18]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 178501053HCID 178501053, compound

Product 1

HCID 178508478HCID 178508478, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred mixture of trans-4-[8-amino-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid methyl ester (150.00 mg, 0.33 mmol) in EtOH (3.00 mL) was added solution of sodium hydroxide (67.8 mg, 1.69 mmol) in H2O (0.500 mL) at 0° C. Then the mixture was stirred at rt. overnight. The solvent was then removed under reduced pressure to give a residue which was dissolved in H2O (3 ml). The solution was acidified to pH 1 by formic acid. The product precipitated out and was collected by filtration and dried on high vacuum pump. 1H NMR (400 MHz, MeOD) δ 1.59-1.88 (m, 4H), 2.03-2.21 (m, 4H), 2.35-2.46 (m, 1H), 3.09-3.20 (m, 1H), 6.99 (d, J=5.1 Hz, 1H), 7.04-7.20 (m, 5H), 7.35-7.45 (m, 2H), 7.53-7.63 (m, 3H). MS (ES+): m/z 428.97 (MH+). HPLC: tR=2.25 min (OpenLynx, polar—5 min).

Workup

  1. customovernight
  2. customThe solvent was then removed under reduced pressure
  3. customto give a residue which
  4. customThe product precipitated out
  5. filtrationwas collected by filtration
  6. customdried on high vacuum pump
  7. customHPLC: tR=2.25 min (OpenLynx, polar—5 min)

Sources & evidence

ORD record
ord-72bf1e8f9a2e48dba144ea4090f8cb35
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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