4-Chloro-beta-methylbenzeneethanamine → (+/-)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[2-(4-chloro-phenyl)-propyl]-4-methyl-benzamide

HRID 1593862Notes

Reaction equation

HRID 1593862 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.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([CH3:34])[CH2:32][NH2:33])=[CH:27][CH:26]=1>>[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:33][CH2:32][CH:31]([C:28]3[CH:27]=[CH:26][C:25]([Cl:24])=[CH:30][CH:29]=3)[CH3:34])=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 1073414-Chloro-beta-methylbenzeneethanamineHCID 687710222-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acid

Product 1

HCID 11613035(+/-)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[2-(4-chloro-phenyl)-propyl]-4-methyl-benzamide

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methyl-benzoic acid was coupled with (±)-2-(4-chloro-phenyl)-propylamine as in EXAMPLE 1, Part C. HPLC: RT=10.22 min. MS (ESI−): mass calcd. for C23H21ClN4O3S2, 500.07; m/z found, 499 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.48 (s, 1H), 8.31 (dd, J=7.0, 1.0, 1H), 8.18 (dd, J=8.8, 1.0, 1H), 7.67 (dd, J=8.8, 7.0, 1H), 7.47 (s, 1H), 7.33-7.27 (m, 2H), 7.16-7.10 (m, 2H), 6.90 (d, J=8.0, 1H), 6.71 (d, J=8.0, 1H), 5.75-5.70 (m, 1H), 3.73-3.62 (m, 1H), 3.30-3.21 (m, 1H), 3.05-2.94 (m, 1H), 2.26 (s, 3H), 1.30 (d, J=7.0, 3H).

Sources & evidence

ORD record
ord-726f4f3ac3af465b89ad8891fa09fe73
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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