Trifluoroacetic acid → HCID 71061456, compound

HRID 2201816Notes

Reaction equation

HRID 2201816 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:13]2[C:14]([NH:18]C(C)(CC(C)(C)C)C)=[N:15][CH:16]=[CH:17][C:12]=2[N:11]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH:10]=1>ClCCl>[NH2:18][C:14]1[C:13]2[C:9]([Cl:8])=[CH:10][N:11]([C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[O:28])[C:12]=2[CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71061467HCID 71061467, compound

Product 1

HCID 71061456HCID 71061456, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.5 mL) was added drop wise to an ice-cooled suspension of benzyl 3-chloro-4-[(2,4,4-trimethylpentan-2-yl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (610 mg) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for about 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 afford benzyl 4-amino-3-chloro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (354.8 mg, 95%) as an 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-af8ac1b4088540778346a1949436c12a
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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