4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → (S)-3-(3-Bromo-4-fluoro-phenyl)-2-[4-chloro-2-(quinoxaline-5-sulfonylamino)-benzoylamino]-propionic acid methyl ester

HRID 1593900Notes

Reaction equation

HRID 1593900 reaction equation
Cl.[CH3:2][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>>[CH3:2][O:3][C:4](=[O:16])[C@@H:5]([NH:6][C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:18]([Cl:17])=[CH:19][C:20]=1[NH:27][S:28]([C:31]1[C:32]2[N:33]=[CH:34][CH:35]=[N:36][C:37]=2[CH:38]=[CH:39][CH:40]=1)(=[O:30])=[O:29])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[CH:9]=1

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 58999897(S)-3-(3-Bromo-4-fluoro-phenyl)-2-[4-chloro-2-(quinoxaline-5-sulfonylamino)-benzoylamino]-propionic acid methyl ester

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. HPLC: RT=10.09 min. MS (ESI−): mass calcd. for C25H19BrClFN4O5S, 621.86; m/z found, 619/621 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.24 (s, 1H), 8.98 (d, J=1.6, 1H), 8.92 (d, J=1.6, 1H), 8.58 (dd, J=7.3, 1.1, 1H), 8.33 (dd, J=8.5, 1.1, 1H), 7.92-7.86 (m, 1H), 7.76 (d, J=1.9, 1H), 7.28-7.25 (m, 1H), 7.19 (d, J=8.4, 1H), 7.06-6.94 (m, 2H), 6.92 (dd, J=8.4, 1.9, 1H), 6.48 (d, J=7.2, 1H), 4.92 (q, J=5.7, 1H), 3.81 (s, 3H), 3.22-3.09 (m, 2H).

Sources & evidence

ORD record
ord-bdbbc81a17ef406fb76df892f4eae079
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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