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

HRID 589775Notes

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)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[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][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

Reactant 2

HCID 244Benzyl Alcohol

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

Product 1

HCID 66800024Benzyl 3-{[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoateYield 68%

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 benzyl alcohol (10.8 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107, using a slightly modified reaction time (2 days). The title compound was obtained in 68% yield (17.6 mg). 1H NMR (500 MHz, CDCl3) δ ppm 2.44 (s, 3 H) 5.31 (s, 2 H) 6.96 (s, 1 H) 7.33-7.40 (m, 5 H) 7.36 (dd, J=8.05, 7.70 Hz, 1 H) 7.43 (ddd, J=8.05, 2.36, 1.20 Hz, 1 H) 7.43 (dd, J=8.63, 2.06 Hz, 1 H) 7.68 (dd, J=8.63, 0.58 Hz, 1 H) 7.69 (dd, J=2.06, 0.58 Hz, 1 H) 7.74 (dd, J=2.36, 1.58 Hz, 1 H) 7.86 (ddd, J=7.70, 1.58, 1.20 Hz, 1 H). MS (ESI+) m/z 472 [M+H]+.

Workup

customa slightly modified reaction time (2 days)

Sources & evidence

ORD record: ord-18733eb3ef6a43e09b45876e0f79166e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

Loading…