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

HRID 2265191Notes

Reaction equation

HRID 2265191 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]([CH3:23])[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]([CH3:23])[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:11])=[O:12])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 548289beta-Amino-4-chlorobenzenepropanolHCID 687710222-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acid

Product 1

HCID 11591660(+/-)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[2-(4-chloro-phenyl)-1-hydroxymethyl-ethyl]-4-methyl-benzamide

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methyl-benzoic acid was coupled with (±)-2-amino-3-(4-chloro-phenyl)-propan-1-ol as in EXAMPLE 1, Part C. HPLC: RT=9.31 min. MS (ESI−): mass calcd. for C23H21ClN4O4S2, 516.07; m/z found, 515 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.52 (s, 1H), 8.33 (dd, J=7.0, 1.0, 1H), 8.19 (dd, J=8.8, 1.0, 1H), 7.68 (dd, J=8.8, 7.0, 1H), 7.48 (s, 1H), 7.32-7.27 (m, 2H), 7.21-7.17 (m, 2H), 7.09 (d, J=8.0, 1H), 6.75 (d, J=8.0, 1H), 6.28 (br d, J=7.4, 1H), 4.32-4.23 (m, 1H), 3.72 (dd, J=10.8, 3.6, 1H), 3.65 (dd, J=10.8, 4.5, 1H), 2.91 (d, J=7.4, 2H), 2.75 (br s, 1H), 2.27 (s, 3H).

Sources & evidence

ORD record
ord-b21ffda42bd141be9effedf31a1b86b3
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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