4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → HCID 11657139, compound

HRID 2265250Notes

Reaction equation

HRID 2265250 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:17])[C@@H:5]([NH2:16])[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([NH:28][S:29]([C:32]2[C:33]3[N:34]=[CH:35][CH:36]=[N:37][C:38]=3[CH:39]=[CH:40][CH:41]=2)(=[O:31])=[O:30])[CH:20]=1>>[CH3:2][O:3][C:4](=[O:17])[C@@H:5]([NH:16][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([Cl:18])=[CH:20][C:21]=1[NH:28][S:29]([C:32]1[C:33]2[N:34]=[CH:35][CH:36]=[N:37][C:38]=2[CH:39]=[CH:40][CH:41]=1)(=[O:31])=[O:30])[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1

Participants

3

Reactant 2

HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acidHCID 68769668HCID 68769668, compound

Product 1

HCID 11657139HCID 11657139, compound

Procedure

3-Benzo[b]thiophen-3-yl-2-(tert-butoxycarbonylamino)-propionic acid was treated as in EXAMPLE 2, Part A, to produce (S)-2-amino-3-benzo[b]thiophen-3-yl-propionic acid methyl ester hydrochloride as a white solid. This ester was coupled to 4-chloro-2-(quinoxaline-5-sulfonylamino)-benzoic acid as in EXAMPLE 1, Part C, to afford the title compound. HPLC: RT=10.33 min. MS (ESI−): mass calcd. for C27H21ClN4O5S2, 580.06; m/z found, 579/581 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.35 (s, 1H), 8.94 (d, J=1.8, 1H), 8.85 (d, J=1.8, 1H), 8.58 (dd, J=7.3, 1.4, 1H), 8.31 (dd, J=8.5, 1.3, 1H), 7.90-7.86 (m, 2H), 7.77 (d, J=2.0, 1H), 7.72-7.70 (m, 1H), 7.37-7.26 (m, 2H), 7.09 (s, 1H), 7.00 (d, J=8.4, 1H), 6.83 (dd, J=8.4, 2.0, 1H), 6.45 (d, J=7.1, 1H), 5.09-5.05 (m, 1H), 3.77 (s, 3H), 3.53 (dd, J=14.7, 5.8, 1H), 3.45 (dd, J=14.8, 5.2, 1H).

Sources & evidence

ORD record
ord-42a34d4b48764dde8d5dfc6ba00d01b2
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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