HCID 178508457, compound → HCID 178511226, compound

HRID 1993264Notes

Reaction equation

HRID 1993264 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 1

HCID 178508457HCID 178508457, compound

Product 1

HCID 178511226HCID 178511226, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 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 conc. 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-316fb793a5df4fecb0cad76e314fbef1
Source dataset
uspto-grants-2010_01
Patent number
US07651687B2

Reaction notes

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