Methanol → HCID 66799823, compound

HRID 589784Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1.CO.N1C=CC=C[CH:28]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([O:19][CH3:28])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

Reactant 3

HCID 887Methanol

HCID 1049Pyridine

HCID 56941307HCID 56941307, compound

Product 1

HCID 66799823HCID 66799823, compoundYield 47%

Procedure

The product was prepared from 3-{[(5-bromo-3-methyl-1-benzothien-2-yl)sulfonyl]-amino}benzoic acid (20.4 mg, 0.048 mmol) (Example 41) and MeOH (50 μL, 1.23 mmol) according to the General Procedure 8, described in Example 119, using different amounts of pyridine (7.5 μL, 0.092 mmol) and a slightly modified reaction volume (0.80 mL). The title compound was obtained in 47% yield (9.9 mg). 1H NMR (500 MHz, CDCl3) δ ppm 2.44 (s, 3H) 3.87 (s, 3 H) 6.94 (s, 1 H) 7.36 (dd, J=8.10, 7.66 Hz, 1 H) 7.41 (ddd, J=8.10, 2.35, 1.26 Hz, 1 H) 7.57 (dd, J=8.63, 1.86 Hz, 1 H) 7.66 (dd, J=8.63, 0.54 Hz, 1 H) 7.73 (dd, J=2.35, 1.51 Hz, 1 H) 7.84 (ddd, J=7.66, 1.51, 1.26 Hz, 1 H) 7.87 (dd, J=1.86, 0.54 Hz, 1 H). MS (ESI+) m/z 440 [M+H]+.

Workup

customa slightly modified reaction volume (0.80 mL)

Sources & evidence

ORD record: ord-d939348121c04f40861bcbffb5d38a3a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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