Pyrrolidine → HCID 136342278, compound

HRID 2204509Notes

Reaction equation

HRID 2204509 reaction equation
Cl.[C:2]1([C@@H:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([NH2:20])[CH2:15]2)[N:6]2[C:7]3[CH:13]=[CH:12][NH:11][C:8]=3[N:9]=[CH:10][C:5]2=[N:4][N:3]=1.C1N=CN([C:26]([N:28]2[CH:32]=N[CH:30]=[CH:29]2)=[O:27])C=1.N1CCC[CH2:34]1>N1C=CC=CC=1>[C:2]1([C@@H:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:26]([N:28]3[CH2:29][CH2:30][CH2:34][CH2:32]3)=[O:27])[CH2:15]2)[N:6]2[C:7]3[CH:13]=[CH:12][NH:11][C:8]=3[N:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 136349099HCID 136349099, compound

Product 1

HCID 136342278HCID 136342278, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a flask containing cis-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclohexanamine hydrochloride (0.050 g, 0.171 mmol, Example #F.1.3) was added CDI (0.030 g, 0.188 mmol) and pyridine (2 mL). The reaction mixture was stirred at ambient temperature for about 16 h. Pyrrolidine (0.016 mL, 0.188 mmol) was added to the reaction mixture and stirred for about 16 h. The solvent was removed under reduced pressure and the crude material was purified by RP-HPLC (Table 2, Method j). The appropriate fractions were combined, the solvent was mostly removed under reduced pressure, and the solid was filtered and dried under lyophilization to give N-(cis-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclohexyl)pyrrolidine-1-carboxamide (0.010 g, 16%): LC/MS (Table 2, Method a) Rt=1.45 min; MS m/z 354 (M+H)+.

Workup

  1. stirringstirred for about 16 h
  2. customThe solvent was removed under reduced pressure
  3. customthe crude material was purified by RP-HPLC (Table 2, Method j)
  4. customthe solvent was mostly removed under reduced pressure
  5. filtrationthe solid was filtered
  6. customdried under lyophilization

Sources & evidence

ORD record
ord-c16f11d649ec48dba90c6fc5400bee77
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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