4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → HCID 45486964, compound

HRID 2265302Notes

Reaction equation

HRID 2265302 reaction equation
Cl.C[O:3][C:4](=[O:16])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[CH:9]=1)[NH2:6].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[C:20]([NH:27][S:28]([C:31]2[C:32]3[N:33]=[CH:34][CH:35]=[N:36][C:37]=3[CH:38]=[CH:39][CH:40]=2)(=[O:30])=[O:29])[CH:19]=1>>[Br:15][C:10]1[CH:9]=[C:8]([CH2:7][C@H:5]([NH:6][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([Cl:17])=[CH:19][C:20]=2[NH:27][S:28]([C:31]2[C:32]3[N:33]=[CH:34][CH:35]=[N:36][C:37]=3[CH:38]=[CH:39][CH:40]=2)(=[O:30])=[O:29])[C:4]([OH:3])=[O:16])[CH:13]=[CH:12][C:11]=1[F:14]

Participants

3

Reactant 2

HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acidHCID 68768499(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride

Product 1

HCID 45486964HCID 45486964, compound

Procedure

The title compound was prepared from 3-bromo-4-fluoro-L-phenylalanine methyl ester hydrochloride and 4-chloro-2-(quinoxaline-5-sulfonylamino)-benzoic acid as in Example 1, Part C, followed by hydrolysis of the resulting methyl ester as in EXAMPLE 2, Part E. HPLC: RT=9.46 min. MS (ESI−): mass calcd. for C24H17BrClFN4O5S, 607.84; m/z found, 605/607 [M−H]−. 1H NMR (400 MHz, acetone-d6): 11.66 (s, 1H), 8.99-8.93 (m, 2H), 8.63-8.57 (m, 1H), 8.37-8.31 (m, 1H), 8.02-7.97 (m, 2H), 7.78-7.75 (m, 1H), 7.65-7.60 (m, 1H), 7.58-7.53 (m, 1H), 7.41-7.34 (m, 1H), 7.24-7.17 (m, 1H), 6.97 (dd, J=8.3, 1.6, 1H), 5.00-4.92 (m, 1H), 3.37-3.28 (m, 1H), 3.18-3.10 (m, 1H).

Sources & evidence

ORD record
ord-b302c48f20f641aa94dae223be7c79b0
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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