Methanol → HCID 66799961, compound

HRID 589785Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]2[S:10][C:9]([S:12]([NH:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([OH:21])=[O:20])(=[O:14])=[O:13])=[C:8]([CH3:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:26]O>>[CH3:1][O:2][C:3]1[C:11]2[S:10][C:9]([S:12]([NH:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([O:21][CH3:26])=[O:20])(=[O:13])=[O:14])=[C:8]([CH3:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 887Methanol

HCID 56941308HCID 56941308, compound

Product 1

HCID 66799961HCID 66799961, compoundYield 71%

Procedure

The product was prepared from 3-{[(7-methoxy-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid (6.8 mg, 0.018 mmol) (Example 42) and MeOH (50 μL, 1.23 mmol) according to the General Procedure 8, described in Example 119. The title compound was obtained in 71% yield (5.0 mg). 1H NMR (500 MHz, CDCl3:DMSO-d6 6:1) δ ppm 2.23 (s, 3 H) 3.56 (s, 3 H) 3.68 (s, 3 H) 6.60 (dd, J=7.54, 1.10 Hz, 1 H) 6.98 (dd, J=8.13, 7.73 Hz, 1H) 7.05 (dd, J=8.17, 1.10 Hz, 1 H) 7.09 (dd, J=8.17, 7.54 Hz, 1 H) 7.14 (ddd, J=8.13, 2.32, 1.09 Hz, 1 H) 7.38 (ddd, J=7.73, 1.63, 1.09 Hz, 1 H) 7.57 (dd, J=2.32, 1.63 Hz, 1 H) 10.18 (s, 1 H). MS (ESI+) m/z 392 [M+H]+.

Sources & evidence

ORD record: ord-eb48392e145b47c9b2156dd6989f90d1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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