1-Propanol → Propyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate

HRID 589776Notes

Reaction equation

HRID 589776 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][CH3:27]>>[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][CH3:27])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

3

Reactant 2

HCID 10311-PropanolHCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid2×

Product 1

HCID 66799853Propyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoateYield 75%

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-propanol (6.0 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107. The title compound was obtained in 75% yield (17.6 mg). 1H NMR (500 MHz, CDCl3) δ ppm 0.97 (t, J=7.45 Hz, 3 H) 1.68-1.77 (m, 2 H) 2.44 (s, 3 H) 4.23 (t, J=6.65 Hz, 2 H) 6.90 (s, 1 H) 7.36 (dd, J=8.05, 7.70 Hz, 1 H) 7.42 (ddd, J=8.05, 2.34, 1.22 Hz, 1 H) 7.44 (dd, J=8.73, 1.95 Hz, 1H) 7.71 (dd, J=8.73, 0.60 Hz, 1 H) 7.71 (dd, J=1.95, 0.60 Hz, 1 H) 7.71 (dd, J=2.34, 1.53 Hz, 1 H) 7.84 (ddd, J=7.70, 1.53, 1.22 Hz, 1 H). MS (ESI+) m/z 424 [M+H]+.

Sources & evidence

ORD record
ord-77283c945f9345eb86aa975d9bc176e5
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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