1-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxamide → HCID 178439457, compound

HRID 2384497Notes

Reaction equation

HRID 2384497 reaction equation
[CH2:1]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([O:17]C)[CH:16]=[C:11]2[C:10]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)=[O:20])=[C:9]1[CH:31]([CH3:33])[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br.CC(O)=O>[CH2:1]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([OH:17])[CH:16]=[C:11]2[C:10]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)=[O:20])=[C:9]1[CH:31]([CH3:33])[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 446084461-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxamide2×

Product 1

HCID 178439457HCID 178439457, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxamide (Compound 9, 7.0 mg, 0.016 mmol) in HBr (48%, 0.5 ml) and HOAc (1.0 ml) was heated to 120° C. for 5 h. The solvent was removed in vacuo and the residue was purified by preparative thin layer chromatography (PTLC) on silica gel (10% MeOH—CH2Cl2) to yield the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative thin layer chromatography (PTLC) on silica gel (10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-48d27918228540b6b6b0772251bcf82c
Source dataset
uspto-grants-2012_09
Patent number
US08263767B2

Reaction notes

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