Dimethylamine → 7-Chloro-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamide

HRID 1272055Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([OH:13])=O)[S:10][C:3]=12.[CH3:14][NH:15][CH3:16].C1COCC1.CCN(CC)CC>>[CH3:14][N:15]([CH3:16])[C:11]([C:9]1[S:10][C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:8]=1)=[O:13]

Participants

Reactant 4

HCID 674Dimethylamine

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 112760337-Chlorothieno[3,2-b]pyridine-2-carboxylic acid

Product 1

HCID 221435377-Chloro-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamideYield 84%

Procedure

was prepared by the reaction of 7-chloro-thieno[3,2-b]pyridine-2-carboxylic acid (0.57 g, 2.67 mmol) with 2.0 M N,N-dimethylamine in THF (1.60 mL, 3.20 mmol) and Et3N (0.447 mL, 3.20 mmol) in a manner as described in Method A to give the desired amide as brown solid (0.54 g, 84%). 1H NMR (300 MHz, CDCl3) δ 8.63 (d, 1H, J=4.85 Hz), 7.74 (s, 1H), 7.35 (d, 1H, J=5.02 Hz), 3.28 (s, 3H), 3.22 (s, 3H); ESIMS (MH+): 240.95.

Sources & evidence

ORD record: ord-700cc275c77d4a77b9b35d00d6e23c84
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208500B2

Reaction notes

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