HCID 178508475, compound → HCID 178511228, compound

HRID 449055Notes

Reaction equation

HRID 449055 reaction equation
C(OC(=O)[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([NH2:27])[C:21]3=[C:20]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:30][CH:29]=3)[N:19]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1>Cl>[NH2:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([NH2:27])[C:21]3=[C:20]([C:28]3[CH:29]=[CH:30][C:31]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:32][CH:33]=3)[N:19]=2)[CH2:14][CH2:13]1

Participants

3

Reactant 1

HCID 178508475HCID 178508475, compound

Product 1

HCID 178511228HCID 178511228, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

trans-{4-[8-Amino-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexylmethyl}-carbamic acid benzyl ester (50.00 mg, 0.091 mmol) was dissolved in concentrated HCl (2.00 mL) at 0° C. The resulting mixture was stirred at rt. overnight. The solution was washed with EtOAc (4×20 ml), the aq. solvent was then removed under reduced pressure to give a crude product which was further purified by flash chromatography (5% MeOH in DCM). 1H NMR (400 MHz, MeOD) δ 1.28-1.46 (m, 2H), 1.74-1.92 (m, 3H), 1.98-2.07 (m, 2H), 2.11-2.20 (m, 2H), 2.90 (d, J=7.1 Hz, 2H), 3.26-3.31 (m, 1H), 7.02-7.28 (m, 6H), 7.40-7.49 (m, 2H), 7.64-7.73 (m, 2H), 7.92 (d, J=5.8 Hz, 1H). MS (ES+): m/z: 414.00 [MH+]. HPLC: tR=1.92 min (OpenLynx, polar—5 min).

Workup

  1. customovernight
  2. washThe solution was washed with EtOAc (4×20 ml)
  3. customthe aq. solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-c8808016fd604ab195b675d5799ab2aa
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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