2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid → HCID 11613520, compound

HRID 2265232Notes

Reaction equation

HRID 2265232 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.Cl.[NH2:25][C@H:26]([CH3:36])[C@H:27]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[OH:28]>>[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:25][C@H:26]([CH3:36])[C@H:27]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[OH:28])=[O:18])(=[O:11])=[O:12])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 160906632-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acidHCID 68771648HCID 68771648, compound

Product 1

HCID 11613520HCID 11613520, compound

Procedure

2-(Benzo[1,2,5]-thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid was coupled with (1S,2R)-2-amino-1-(4-chloro-phenyl)-propan-1-ol hydrochloride as in EXAMPLE 1, Part C. HPLC: RT=10.17 min. MS (ESI−): mass calcd. for C22H18Cl2N4O4S2, 536.01; m/z found, 535/537 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.64 (s, 1H), 8.39 (dd, J=7.0, 1.0, 1H), 8.23 (dd, J=8.8, 1.0, 1H), 7.73 (dd, J=8.8, 7.0, 1H), 7.72 (d, J=2.0, 1H), 7.38-7.33 (m, 2H), 7.33-7.28 (m, 2H), 7.24 (d, J=8.5, 1H), 6.95 (dd, J=8.4, 2.0, 1H), 6.22 (br d, J=8.1, 1H), 4.97 (d, J=2.9, 1H), 4.42 (ddq, J=8.3, 7.0, 2.9, 1H), 1.04 (d, J=6.9, 3H).

Sources & evidence

ORD record
ord-9e6d7dc899a74b6089c7daa2bc07aa33
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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