Trifluoroacetic acid → benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 2201795Notes

Reaction equation

HRID 2201795 reaction equation
FC(F)(F)C(O)=O.CC([NH:16][C:17]1[C:22]2[CH:23]=[CH:24][N:25]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[C:21]=2[CH:20]=[CH:19][N:18]=1)(CC(C)(C)C)C>ClCCl>[NH2:16][C:17]1[C:22]2[CH:23]=[CH:24][N:25]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[C:21]=2[CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71061424benzyl 4-[(2,4,4-trimethylpentan-2-yl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 71061834benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added drop wise to an ice-cooled suspension of benzyl 4-[(2,4,4-trimethylpentan-2-yl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (5 g, 9.7 mmol, Step c) in dichloromethane (30 mL). The reaction mixture was stirred at room temperature for 4 hours. Upon completion, the reaction mixture was concentrated under vacuum and the residue was stirred in excess aqueous ammonia solution. The precipitated solid was filtered under suction, washed with water and dried to yield benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.5 g, 95%) as off-white solid.

Workup

  1. temperaturecooled
  2. concentrationUpon completion, the reaction mixture was concentrated under vacuum
  3. stirringthe residue was stirred in excess aqueous ammonia solution
  4. filtrationThe precipitated solid was filtered under suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5350527cfb6141848b5de12fc503520f
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

Loading…