beta-Amino-4-chlorobenzenepropanol → (+/-)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-[2-(4-chloro-phenyl)-1-hydroxymethyl-ethyl]-benzamide

HRID 2265224Notes

Reaction equation

HRID 2265224 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16](O)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[NH2:24][CH:25]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[CH2:26][OH:27]>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16]([NH:24][CH:25]([CH2:26][OH:27])[CH2:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 548289beta-Amino-4-chlorobenzenepropanolHCID 160906632-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid

Product 1

HCID 11577418(+/-)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-[2-(4-chloro-phenyl)-1-hydroxymethyl-ethyl]-benzamide

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid was coupled with (±)-2-amino-3-(4-chloro-phenyl)-propan-1-ol as in EXAMPLE 1, Part C. HPLC: RT=9.71 min. MS (ESI−): mass calcd. for C22H18Cl2N4O4S2, 536.01; m/z found, 535/537 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.57 (s, 1H), 8.38 (br d, J=6.2, 1H), 8.22 (br d, J=8.4, 1H), 7.71 (br m, 2H), 7.35-7.10 (br m, 5H), 6.92 (br d, J=6.0, 1H), 6.30 (br m, 1H), 4.36-4.27 (br m, 1H), 3.76-3.62 (br m, 2H), 2.98-2.85 (br m, 2H), 1.92 (br s, 1H).

Sources & evidence

ORD record
ord-c002a15b4c5a4b5b9934230e48cdf470
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

Loading…