Triethylamine → 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxamide

HRID 2206046Notes

Reaction equation

HRID 2206046 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]([O:14][CH3:15])[NH:8][CH:9]=[C:10]([C:11](O)=[O:12])[C:5]=2[N:4]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]=1.C([N:23](CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(#N)C>[Br:1][C:2]1[C:6]2[CH:7]([O:14][CH3:15])[NH:8][CH:9]=[C:10]([C:11]([NH2:23])=[O:12])[C:5]=2[N:4]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1179880413-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

Product 1

HCID 1179878843-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (894 mg), HOBt ammonium salt (1155 mg) and triethylamine (1.41 mL) in acetonitrile (8 mL) was added EDCI hydrochloride (1179 mg), and the mixture was stirred overnight. The reaction mixture was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (654 mg).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74dae1c3cc85423f9a7b706411087afe
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…