3-(Dimethylamino)-1-propanol → HCID 66799724, compound

HRID 589782Notes

Reaction equation

HRID 589782 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.[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29]O>>[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][CH2:29][CH2:28][CH2:27][N:26]([CH3:31])[CH3:25])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

3

Reactant 2

HCID 766463-(Dimethylamino)-1-propanolHCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid2×

Product 1

HCID 66799724HCID 66799724, compoundYield 99%

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 3-dimethylamino-1-propanol (10.3 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107. The title compound was obtained in 99% yield (25.5 mg). 1H NMR (500 MHz, CDCl3) δ ppm 2.19-2.27 (m, 2 H) 2.53 (s, 3 H) 2.86 (s, 6 H) 3.19-3.25 (m, 2 H) 4.30-4.36 (m, 2 H) 7.35 (dd, J=8.12, 7.78 Hz, 1 H) 7.42 (dd, J=8.67, 2.05 Hz, 1 H) 7.56 (ddd, J=8.12, 2.34, 1.05 Hz, 1 H) 7.70 (dd, J=8.67, 0.57 Hz, 1 H) 7.71 (dd, J=2.05, 0.57 Hz, 1H) 7.75 (ddd, J=7.78, 1.60, 1.05 Hz, 1 H) 7.89 (dd, J=2.34, 1.60 Hz, 1 H) 8.38 (br. s., 1 H). MS (ESI+) m/z 467 [M+H]+.

Sources & evidence

ORD record
ord-d2348b16ca6f4ea7b5b0537f15986b9c
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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