HCID 178420346, compound → HCID 178511502, compound

HRID 1969906Notes

Reaction equation

HRID 1969906 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][NH:24][C:21]=4[N:22]=[CH:23][C:18]3=[N:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH:26]1[C:20]2[N:19]3[C:15]([C@@H:12]4[CH2:11][CH2:10][C@H:9]([NH2:8])[CH2:14][CH2:13]4)=[CH:16][N:17]=[C:18]3[CH:23]=[N:22][C:21]=2[NH:24][CH:25]=1

Participants

4

Reactant 1

HCID 178420346HCID 178420346, compound

Product 1

HCID 178511502HCID 178511502, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of (cis)-N,N-dibenzyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclohexanamine (1.0 g, 2.3 mmol) in EtOH (30 mL) was added Pd(OH)2 on carbon (0.64 g, 0.46 mmol) and the resulting mixture was shaken under hydrogen pressure of about 30 psi on a Parr shaker at about 50° C. for about 7 h. The catalyst was filtered off using a pad of Celite® and the filtrate was concd under reduced pressure. The material was purified by chiral chromatography (Table 2, method 34). The collected fractions were combined, concd under reduced pressure and chased with EtOH (20 mL). The resulting solid was dried in a heated vacuum oven at about 60° C. to yield (cis)-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclohexanamine (0.353 g, 60%) as a white solid: LC/MS (Table 1, Method a) Rt=0.85 min; MS m/z 256 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. customThe material was purified by chiral chromatography (Table 2, method 34)
  3. customThe resulting solid was dried in a heated vacuum oven at about 60° C.

Sources & evidence

ORD record
ord-2f30b963da1a4b39a2fdde29bd640d83
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…