2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acid → HCID 11498441, compound

HRID 2265258Notes

Reaction equation

HRID 2265258 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]([I: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.[NH2:25][C@H:26]([CH3:36])[C@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Br:35])[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]([I: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][CH:32]=[C:31]([Br:35])[CH:30]=3)[OH:28])=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 160906642-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acidHCID 68772630HCID 68772630, compound

Product 1

HCID 11498441HCID 11498441, compound

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodobenzoic acid was coupled with (1S,2R)-2-amino-1-(3-bromo-phenyl)-propan-1-ol hydrochloride salt (EXAMPLE 108, Part E) as in Example 1, Part C (11 mg, 16%). HPLC: RT=10.19 min. MS (ESI−): mass calcd. for C22H18BrIN4O4S2, 673.34; m/z found, 671/673 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.45 (s, 1H), 8.37 (d, J=7.0, 1H), 8.23 (d, J=8.8, 1H), 8.08 (d, J=1.5, 1H), 7.73 (dd, J=8.8, 7.1, 1H), 7.55-7.53 (m, 1H), 7.47-7.43 (m, 1H), 7.33 (dd, J=8.2, 1.5, 1H), 7.31-7.21 (m, 3H), 6.99 (d, J=8.3, 1H), 6.19 (d, J=8.6, 1H), 4.95-4.94 (m, 1H), 4.44-4.40 (m, 1H), 2.60 (s, 1H), 1.03 (d, J=6.9, 3H).

Sources & evidence

ORD record
ord-88b2babe8fed4e01952bb2d65bb51e3b
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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