2-Aminoindane → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-indan-2-yl-benzamide

HRID 2265223Notes

Reaction equation

HRID 2265223 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]([OH:18])=O)(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[NH2:24][CH:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26]1>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16]([NH:24][CH:25]3[CH2:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26]3)=[O:18])(=[O:11])=[O:12])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 763102-AminoindaneHCID 160906632-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid

Product 1

HCID 116054782-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-indan-2-yl-benzamide

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid was coupled with 2-aminoindane as in EXAMPLE 1, Part C. HPLC: RT=10.24 min. MS (ESI−): mass calcd. for C22H17ClN4O3S2, 484.04; m/z found, 483 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.64 (s, 1H), 8.37 (dd, J=7.0, 1.0, 1H), 8.23 (dd, J=8.8, 1.0, 1H), 7.72 (dd, J=8.8, 7.0, 1H), 7.72 (d, J=2.0, 1H), 7.28-7.19 (m, 4H), 7.14 (d, J=8.4, 1H), 6.89 (dd, J=8.4, 2.0, 1H), 6.12 (br d, J=7.5, 1H), 4.87-4.80 (m, 1H), 3.41 (dd, J=16.3, 7.0, 2H), 2.83 (dd, J=16.3, 3.9, 2H).

Sources & evidence

ORD record
ord-69ad98e70b274651ab0b20d834533292
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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