N-Methylbenzeneethanamine → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-N-methyl-N-Phenethyl-benzamide

HRID 2265214Notes

Reaction equation

HRID 2265214 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]([Br: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.[CH3:24][NH:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:15]=3[C:16]([N:25]([CH3:24])[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:17])(=[O:11])=[O:12])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 11503N-MethylbenzeneethanamineHCID 160907442-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acid

Product 1

HCID 115628022-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-N-methyl-N-Phenethyl-benzamide

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acid was coupled with N-methylphenethylamine as in EXAMPLE 1, Part C. HPLC: RT=9.90 min. MS (ESI−): mass calcd. for C22H19BrN4O3S2, 530.01; m/z found, 529/531 [M−H]−. 1H NMR (400 MHz, CDCl3; rotameric broadening): 8.95-8.80 (br s, 0.6H), 8.57-8.43 (br s, 0.4H), 8.27 (dd, J=7.0, 0.9, 1H), 8.23 (br d, J=8.8, 1H), 7.80-7.64 (m, 2H), 7.37-6.85 (br m, 6H), 6.73-6.62 (br m, 0.6H), 6.55-6.40 (br m, 0.4H), 3.68-3.35 (br m, 1.3H), 3.35-3.07 (br m, 0.7H), 3.07-2.25 (br m, 5H).

Sources & evidence

ORD record
ord-3025e443d60a4ce5a4cc7e2f1d5ff6d2
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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