Oxalyl chloride → HCID 20767918, compound

HRID 985305Notes

Reaction equation

HRID 985305 reaction equation
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[S:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:19][C:20]3[CH:32]=[CH:31][C:23]4[C:24]([C:28]([OH:30])=O)=[C:25]([CH3:27])[O:26][C:22]=4[CH:21]=3)[CH:11]=2)=[O:9])[CH2:4]1.C(Cl)(=O)C(Cl)=O.[NH2:39][CH2:40][CH:41]1[CH2:43][CH2:42]1>>[CH:41]1([CH2:40][NH:39][C:28]([C:24]2[C:23]3[CH:31]=[CH:32][C:20]([O:19][C:16]4[CH:15]=[CH:14][N:13]=[C:12]5[CH:11]=[C:10]([C:8]([N:5]6[CH2:6][CH2:7][CH:3]([O:2][CH3:1])[CH2:4]6)=[O:9])[S:18][C:17]=45)=[CH:21][C:22]=3[O:26][C:25]=2[CH3:27])=[O:30])[CH2:43][CH2:42]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 75646CyclopropanemethanamineHCID 22143552HCID 22143552, compound

Product 1

HCID 20767918HCID 20767918, compound

Procedure

This material was prepared from 6-[2-(3-methoxypyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-2-methyl-benzofuran-3-carboxylic acid 89e by treatment with oxalyl chloride and (aminomethyl)cyclopropane in a manner as previously described for example 16d. 1H NMR (DMSO-d6) δ8.55 (1H, d, J=5.1 Hz), 8.20 (1H, s), 8.05 (1H, s), 7.80 (1H, d, J=8.6 Hz), 7.64 (1H, s), 7.22 (1H, d, J=8.3 Hz), 6.69 (1H, d, J=5.3 Hz), 4.10-3.80 (3H, m), 3.70-3.50 (2H, m), 3.26 (3H, d, J=12.6 Hz), 3.15 (2H, m), 2.63 (3H, s), 2.20-1.95 (2H, m), 1.08 (1H, m), 0.45 (2H, d, J=7.1 Hz), 0.25 (2H, d, J=4.3 Hz).

Sources & evidence

ORD record
ord-b8967dff80bf47dfa4d99b6297598cb6
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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