Hydrochloric Acid → HCID 178511226, compound

HRID 2042355Notes

Reaction equation

HRID 2042355 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:20]3[CH2:25][CH2:24][C@H:23]([CH2:26][NH:27]C(=O)OCC4C=CC=CC=4)[CH2:22][CH2:21]3)=[N:9][C:10]=2[C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:6][N:7]=1.Cl>O>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:20]3[CH2:21][CH2:22][C@H:23]([CH2:26][NH2:27])[CH2:24][CH2:25]3)=[N:9][C:10]=2[C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178508457HCID 178508457, compound

Product 1

HCID 178511226HCID 178511226, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of benzyl {[trans-4-(8-amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methyl}carbamate (0.163 g, 0.330 mmol) in cone. HCl (5 ml) was stirred at rt overnight. The reaction mixture was diluted with H2O (20 mL), washed with Et2O (30 mL), then basified with 1N NaOH (aq) and extracted with DCM (3×20 mL). The combined extracts were washed with water then dried over Na2SO4 and concentrated in vacuo To afford 0.085 g of desired compound. MS (ES+): m/z 361.30 [MH+].

Workup

  1. washwashed with Et2O (30 mL)
  2. extractionextracted with DCM (3×20 mL)
  3. washThe combined extracts were washed with water
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e607c77c5da0499b901392b5a46cd8ca
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

Loading…