Methanol → HCID 66799754, compound

HRID 589786Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[S:9][C:8]([S:11]([NH:14][C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([OH:20])=[O:19])(=[O:13])=[O:12])=[C:7]([CH3:24])[C:6]=2[CH:5]=[CH:4][CH:3]=1.CO.[C:27](N1C=CN=C1)(N1C=CN=C1)=O>>[Cl:1][C:2]1[C:10]2[S:9][C:8]([S:11]([NH:14][C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18]([O:20][CH3:27])=[O:19])(=[O:12])=[O:13])=[C:7]([CH3:24])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 887Methanol

HCID 682631,1'-Carbonyldiimidazole

HCID 56941310HCID 56941310, compound

Product 1

HCID 66799754HCID 66799754, compoundYield 74%

Procedure

The product was prepared from 3-{[(7-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid (9.2 mg, 0.024 mmol) (Example 44) and MeOH (50 μL, 1.23 mmol) according to the General Procedure 8, described in Example 119, using a different amount of 1,1′-carbonyldiimidazole (10.0 mg, 0.0621 mmol). The title compound was obtained in 74% yield (7.0 mg). 1H NMR (500 MHz, CDCl3) δ ppm 2.46 (s, 3 H) 3.87 (s, 3 H) 6.79 (s, 1 H) 7.37 (dd, J=8.06, 7.70 Hz, 1 H) 7.41 (dd, J=8.06, 7.69 Hz, 1 H) 7.43 (ddd, J=8.06, 2.32, 1.21 Hz, 1 H) 7.48 (dd, J=7.69, 0.98 Hz, 1 H) 7.65 (dd, J=8.06, 0.98 Hz, 1 H) 7.74 (dd, J=2.32, 1.51 Hz, 1 H) 7.84 (ddd, J=7.70, 1.51, 1.21 Hz, 1 H). MS (ESI+) m/z 396 [M+H]+.

Sources & evidence

ORD record: ord-1a0a864bfbd24914b80784782fbe807f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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