1-Butanol → Butyl 3-{[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoate

HRID 589774Notes

Reaction equation

HRID 589774 reaction equation
[Cl: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.[CH2:25](O)[CH2:26][CH2:27][CH3:28]>>[Cl: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][CH2:25][CH2:26][CH2:27][CH3:28])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

3

Reactant 2

HCID 2631-ButanolHCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid2×

Product 1

HCID 66800176Butyl 3-{[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoateYield 77%

Procedure

The product was prepared from 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid (21 mg, 0.055 mmol) (Intermediate 19) and 1-butanol (7.4 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107. The title compound was obtained in 77% yield (18.5 mg). 1H NMR (500 MHz, CDCl3) δ ppm 0.95 (t, J=7.39 Hz, 3 H) 1.37-1.46 (m, 2 H) 1.65-1.72 (m, 2 H) 2.44 (s, 3 H) 4.27 (t, J=6.65 Hz, 2H) 6.88 (s, 1 H) 7.36 (dd, J=8.06, 7.67 Hz, 1 H) 7.42 (ddd, J=8.06, 2.32, 1.22 Hz, 1 H) 7.45 (dd, J=8.67, 1.95 Hz, 1 H) 7.71 (dd, J=8.67, 0.52 Hz, 1 H) 7.70-7.71 (m, 1 H) 7.71 (dd, J=1.95, 0.52 Hz, 1 H) 7.84 (ddd, J=7.67, 1.50, 1.21 Hz, 1 H). MS (ESI+) m/z 438 [M+H]+.

Sources & evidence

ORD record
ord-59f6074d64534421859c014f528b5a65
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

Loading…