4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → HCID 49804966, compound

HRID 2265248Notes

Reaction equation

Cl.C[O:3][C:4](=[O:16])[C@@H:5]([NH2:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=1.[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>>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:15][C@@H:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=2)[C:4]([OH:3])=[O:16])=[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:29])=[O:30])[CH:19]=1

Participants

Reactant 2

HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid

HCID 22870234HCID 22870234, compound

Product 1

HCID 49804966HCID 49804966, compound

Procedure

(S)-2-(tert-Butoxycarbonylamino)-3-(3-cyano-phenyl)-propionic acid was treated as in EXAMPLE 2, Part A, to produce (S)-2-amino-3-(3-cyano-phenyl)-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. The resulting methyl ester was hydrolyzed as in EXAMPLE 2, Part E, to afford the title compound. HPLC: RT=8.94 min. MS (ESI−): mass calcd. for C25H18ClN5O5S, 535.07; m/z found, 534/536 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.01 (s, 1H), 9.03 (d, J=1.7, 1H), 8.94 (d, J=1.7, 1H), 8.57 (d, J=7.4, 1H), 8.33 (d, J=8.5, 1H), 7.90 (t, 7.5, 1H), 7.74 (d, J=1.9, 1H), 7.57-7.55 (m, 1H), 7.47-7.41 (m, 3H), 7.12 (d, J=8.4, 1H), 6.93 (dd, J=5.6, 1.9, 1H), 6.40 (d, J=7.3, 1H), 5.02-4.98 (m, 1H), 3.36 (dd, J=14.1, 6.0, 1H), 3.25 (dd, J=14.2, 5.6, 1H).

Sources & evidence

ORD record: ord-cb6121cea31649f9a868207edfad668f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855292B2

Reaction notes

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