Water → HCID 178487936, compound

HRID 449056Notes

Reaction equation

HRID 449056 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)=[C:30]([O:41][CH3:42])[CH:29]=3)[N:19]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1.O>Cl>[NH2:10][CH2:11][C@H:12]1[CH2:13][CH2:14][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)=[C:30]([O:41][CH3:42])[CH:29]=3)[N:19]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 962WaterHCID 178487938HCID 178487938, compound

Product 1

HCID 178487936HCID 178487936, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

trans-{4-[8-Amino-1-(3-methoxy-4-phenoxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexylmethyl}-carbamic acid benzyl ester (80 mg, 0.0001 mol) was dissolved in conc. HCl (3 mL) at 0° C. The resulting mixture was allowed to stir at rt overnight. LCMS indicates the reaction is over. Water was added to the reaction mixture and the mixture was extracted with EtOAc. The aq. phase was concentrated in vacuo to give a residue which was purified by flash chromatography (eluted by 10% MeOH in DCM). 1H NMR (400 MHz, CDCl3) δ 1.08 (dd, J=12.13, 3.28 Hz, 2H) 1.74-1.89 (m, 2H) 1.90-1.98 (m, 2H) 2.00-2.09 (m, 2H) 2.57 (d, J=6.57 Hz, 2H) 2.78-2.90 (m, 1H) 3.83 (s, 3H) 6.89-6.95 (m, 2H) 6.95-7.04 (m, 3H) 7.09 (dd, J=8.21, 1.89 Hz, 1H) 7.16 (d, J=5.05 Hz, 1H) 7.21-7.28 (m, 3H). MS (ES+): m/z: 444.17 [MH+]. HPLC: tR=1.88 min (OpenLynx: polar—5 min).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. concentrationThe aq. phase was concentrated in vacuo
  3. customto give a residue which
  4. customwas purified by flash chromatography (eluted by 10% MeOH in DCM)
  5. customHPLC: tR=1.88 min (OpenLynx: polar—5 min)

Sources & evidence

ORD record
ord-1e6e10ca502f4e8880493623afb74412
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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