2-Phenoxyethanamine → 5-Chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (2-phenoxyethyl)amide

HRID 1693435Notes

Reaction equation

HRID 1693435 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([OH:13])=O)[NH:10][C:5]2=[CH:4][CH:3]=1.[O:14]([CH2:21][CH2:22][NH2:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[O:14]([CH2:21][CH2:22][NH:23][C:11]([C:9]1[NH:10][C:5]2[C:6](=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:8]=1)=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 156512-PhenoxyethanamineHCID 116655855-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

Product 1

HCID 113476165-Chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (2-phenoxyethyl)amide

Procedure

The title compound was prepared as outlined in EXAMPLE 1 from 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (Preparation 6) and 2-phenoxyethylamine. On completion of the reaction, the mixture was partitioned between water and dichloromethane on a hydrophobic frit, washing with dichloromethane. The organic filtrate was concentrated in vacuo then triturated with dichloromethane/methanol/ethyl acetate to give the title compound as a white solid. δH (d6 DMSO): 3.68 (2H, m), 4.13 (2H, m), 6.94 (3H, m), 7.25 (4H, m), 7.83 (1H, d), 8.95 (1H, t), 12.09 (1H, s). m/z (ES+)=316 [M+H]+; RT=3.45 min.

Workup

  1. customThe title compound was prepared
  2. customOn completion of the reaction
  3. customthe mixture was partitioned between water and dichloromethane on a hydrophobic frit
  4. washwashing with dichloromethane
  5. concentrationThe organic filtrate was concentrated in vacuo
  6. customthen triturated with dichloromethane/methanol/ethyl acetate

Sources & evidence

ORD record
ord-c5a70c631e9040618f3a49a377666844
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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