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

HRID 1593883Notes

Reaction equation

HRID 1593883 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[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:40])[C@@H:29]([NH2:39])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[C:33]([Br:38])[CH:32]=1>>[CH3:26][O:27][C:28](=[O:40])[C@@H:29]([NH:39][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I: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[CH:36]=[CH:35][C:34]([F:37])=[C:33]([Br:38])[CH:32]=1

Participants

3

Reactant 2

HCID 160907584-Iodo-2-(quinoxaline-5-sulfonylamino)benzoic acidHCID 68768499(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride

Product 1

HCID 58999870(S)-3-(3-Bromo-4-fluoro-phenyl)-2-[4-iodo-2-(quinoxaline-5-sulfonylamino)-benzoylamino]-propionic acid methyl ester

Procedure

4-Iodo-2-(quinoxaline-5-sulfonylamino)-benzoic acid was coupled to (S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride as in EXAMPLE 1, Part C, to afford the title compound. HPLC: RT=10.30 min. MS (ESI+): mass calcd. for C25H19BrFIN4O5S, 713.32; m/z found, 713/715 [M+H]+. 1H NMR (500 MHz, CDCl3): 11.09 (s, 1H), 8.99 (d, J=1.7, 1H), 8.92 (d, J=1.7, 1H), 8.58 (dd, J=7.3, 1.3, 1H), 8.33 (dd, J=8.5, 1.3, 1H), 8.09 (d, J=1.5, 1H), 7.90 (dd, J=8.3, 7.5, 1H), 7.30 (dd, J=8.2, 1.5, 1H), 7.25-7.23 (m, 1H), 7.05-6.98 (m, 1H), 6.98-6.90 (m, 2H), 6.43 (d, J=7.1, 1H), 4.90 (q, J=5.5, 1H), 3.81 (s, 3H), 3.20-3.08 (m, 2H).

Sources & evidence

ORD record
ord-6ed936b26e794e0d8d1608ce40fbf480
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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