1-(((2-(Methylsulfonyl)ethoxy)carbonyl)oxy)-2,5-pyrrolidinedione → [5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-carbamic acid 2-methanesulfonyl-ethyl ester

HRID 2053442Notes

Reaction equation

HRID 2053442 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:24])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([Cl:23])=[CH:12][CH:11]=3)[O:4][N:3]=1.[CH3:25][S:26]([CH2:29][CH2:30][O:31][C:32](=O)[O:33]N1C(=O)CCC1=O)(=[O:28])=[O:27]>>[CH3:25][S:26]([CH2:29][CH2:30][O:31][C:32](=[O:33])[NH:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:24])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([Cl:23])=[CH:12][CH:11]=3)[O:4][N:3]=1)(=[O:28])=[O:27]

Participants

3

Reactant 2

HCID 3885501-(((2-(Methylsulfonyl)ethoxy)carbonyl)oxy)-2,5-pyrrolidinedioneHCID 1355311763-(3-Amino-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one

Product 1

HCID 135440177[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-carbamic acid 2-methanesulfonyl-ethyl ester

Procedure

This was prepared according to Example 64 from 3-(3-amino-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-methanesulfonyl-ethyl ester. 1H NMR (400 MHz, DMSO-d6) δ 12.62 (s, 1H), 10.78 (s, 1H), 7.66 (dd, 1H), 7.48 (m, 4H), 7.32 (m, 2H), 6.96 (d, 1H), 6.89 (s, 1H), 4.42 (t, 2H), 3.56 (t, 2H), 3.12 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C22H18ClN3O6S 487.0, found 488.0 (M+H).

Workup

  1. customThis was prepared

Sources & evidence

ORD record
ord-7eae02e180ce446a8ea6b837be6e86e2
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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