4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → HCID 11577934, compound

HRID 2265249Notes

Reaction equation

HRID 2265249 reaction equation
Cl.C[O:3][C:4](=[O:17])[CH2:5][C@@H:6]([NH2:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([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:20]=1>>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:16][C@@H:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:5][C:4]([OH:3])=[O:17])=[O:24])=[C:21]([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:30])=[O:31])[CH:20]=1

Participants

3

Reactant 2

HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acidHCID 68773138HCID 68773138, compound

Product 1

HCID 11577934HCID 11577934, compound

Procedure

(S)-3-(tert-Butoxycarbonylamino)-4-(3,4-dichloro-phenyl)-butyric acid was treated as in EXAMPLE 2, Part A, to produce (S)-3-amino-4-(3,4-dichloro-phenyl)-butyric 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. HPLC: RT=9.78 min. MS (ESI−): mass calcd. for C25H19Cl3N4O5S, 592.01; m/z found, 593/595 [M−H]−. 1H NMR (500 MHz, CD3OD): 8.97 (d, J=1.8, 1H), 8.93 (d, J=1.8, 1H), 8.55 (dd, J=7.4, 1.3, 1H), 8.33 (dd, J=8.5, 1.3, 1H), 7.97-7.94 (m, 1H), 7.69 (d, J=2.0, 1H), 7.42 (d, J=8.2, 1H), 7.38-7.36 (m, 2H), 7.16 (dd, J=8.2, 2.0, 1H), 6.97 (dd, J=8.6, 2.0, 1H), 4.56-4.50 (m, 1H), 2.90 (dd, J=13.7, 6.1, 1H), 2.81 (dd, J=13.7, 7.7, 1H), 2.54 (dd, J=15.9, 6.2, 1H), 2.45 (dd, J=15.9, 7.4, 1H).

Sources & evidence

ORD record
ord-5cedc1e5cafe4b45bf5614ace4673530
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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