Oxalyl chloride → HCID 20767911, compound

HRID 985304Notes

Reaction equation

HRID 985304 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.[CH:39]1([NH2:42])[CH2:41][CH2:40]1>>[CH:39]1([NH:42][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])[CH2:41][CH2:40]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 22143552HCID 22143552, compound

Product 1

HCID 20767911HCID 20767911, compoundYield 33.1%

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 (37 mg, 0.08 mmole) by treatment with oxalyl chloride (15 μl, 0.17 mmole) and cyclopropylamine (56 μl, 0.81 mmole) in a manner as previously described for example 16d to give a white solid (13 mg,33%). 1H NMR (DMSO-d6) δ8.57 (1H, d, J=5.1 Hz), 8.19 (1H, s), 8.06 (1H, bs), 7.74 (1H, d, J=6.1 Hz), 7.65 (1H, s), 7.24 (1H, d, J=6.1 Hz), 6.71 (1H, d, J=1.8 Hz), 4.10-3.80 (3H, m), 3.70-3.35 (2H, m), 3.25 (3H, d, J=13.1 Hz), 2.86 (1H, m), 2.59 (3H, s), 2.25-1.95 (2H, m), 0.71 (2H, m), 0.60 (2H, m).

Sources & evidence

ORD record
ord-353c47aa643348e599f72e9650c3cd9a
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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