Quinoxaline-5-sulfonyl chloride → (S)-3-(3-Bromo-4-fluoro-phenyl)-2-[4,5-dichloro-2-(quinoxaline-5-sulfonylamino)-benzoylamino]-propionic acid methyl ester

HRID 1593901Notes

Reaction equation

HRID 1593901 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[C:26]([Cl:27])=[CH:25][C:21]([C:22](O)=[O:23])=[C:20]([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:19]=1.N1C2C=CC=C(S(Cl)(=O)=O)C=2N=CC=1>>[CH3:2][O:3][C:4](=[O:16])[C@@H:5]([NH:6][C:22](=[O:23])[C:21]1[CH:25]=[C:26]([Cl:27])[C:18]([Cl:17])=[CH:19][C:20]=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])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[CH:9]=1

Participants

4

Reactant 3

HCID 16090697Quinoxaline-5-sulfonyl chlorideHCID 160907694,5-Dichloro-2-(quinoxaline-5-sulfonylamino)-benzoic acidHCID 68768499(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride

Product 1

HCID 45486947(S)-3-(3-Bromo-4-fluoro-phenyl)-2-[4,5-dichloro-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 4,5-dichloro-2-(quinoxaline-5-sulfonylamino)-benzoic acid (prepared from quinoxaline-5-sulfonyl chloride as in EXAMPLE 14, Part A) as in Example 1, Part C. HPLC: RT=10.50 min. MS (ESI−): mass calcd. for C25H18BrCl2FN4O5S, 656.31; m/z found, 653/655/657 [M−H]−. 1H NMR (400 MHz, CDCl3): 10.99 (s,1H), 8.96 (d, J=1.7, 1H), 8.93 (d, J=1.7, 1H), 8.55 (dd, J=7.3, 1.1, 1H), 8.33 (dd, J=8.5, 1.1, 1H), 7.91-7.85 (m, 2H), 7.31-7.22 (m, 2H), 7.07-6.94 (m, 2H), 6.52 (d, J=7.3, 1H), 4.89 (q, J=5.8, 1H), 3.81 (s, 3H), 3.21-3.08 (m, 2H).

Sources & evidence

ORD record
ord-9072aa31c8b448f2a62251108775127f
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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