4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → HCID 11606891, compound

HRID 2265184Notes

Reaction equation

HRID 2265184 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([NH:11][S:12]([C:15]2[C:16]3[N:17]=[CH:18][CH:19]=[N:20][C:21]=3[CH:22]=[CH:23][CH:24]=2)(=[O:14])=[O:13])[CH:3]=1.Cl.[CH3:26][O:27][C:28](=[O:38])[C@@H:29]([NH2:37])[CH2:30][C:31]1[S:32][C:33]([Br:36])=[CH:34][CH:35]=1>>[CH3:26][O:27][C:28](=[O:38])[C@@H:29]([NH:37][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[NH:11][S:12]([C:15]1[C:16]2[N:17]=[CH:18][CH:19]=[N:20][C:21]=2[CH:22]=[CH:23][CH:24]=1)(=[O:14])=[O:13])[CH2:30][C:31]1[S:32][C:33]([Br:36])=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acidHCID 68771710HCID 68771710, compound

Product 1

HCID 11606891HCID 11606891, compound

Procedure

4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid was coupled with (S)-2-amino-3-(5-bromo-thiophen-2-yl)-propionic acid methyl ester hydrochloride as in EXAMPLE 1, Part C. HPLC: RT=10.34 min. MS (ESI−): mass calcd. for C23H18BrClN4O5S2, 607.96; m/z found, 607/609 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.31 (s, 1H), 8.94 (d, J=1.8, 1H), 8.91 (d, J=1.8, 1H), 8.59 (dd, J=7.4, 1.4, 1H), 8.32 (dd, J=8.4, 1.3, 1H), 7.89 (dd, J=8.4, 7.4, 1H), 7.80 (d, J=2.0, 1H), 7.27 (d, J=8.4, 1H), 6.96 (dd, J=8.4, 2.0, 1H), 6.86 (d, J=3.7, 1H), 6.57 (br d, J=6.8, 1H), 6.48 (d, J=3.6, 1H), 4.92 (dt, J=7.0, 4.6, 1H), 3.83 (s, 3H), 3.40 (d, J=4.6, 2H).

Sources & evidence

ORD record
ord-df9646196d534496807166d915e0250a
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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