m-Chloroperbenzoic acid → 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamide

HRID 1806563Notes

Reaction equation

HRID 1806563 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:34][CH3:35])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:22]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)=[O:23])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:36].C1C=C(Cl)C=C(C(OO)=[O:45])C=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:34]([CH3:35])=[O:45])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:22]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)=[O:23])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:36]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 21226206Ethyl acetate hexaneHCID 59212685HCID 59212685, compound

Product 1

HCID 574345493-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamideYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamide (1.65 g, 3.16 mmol) in DCM (53 mL) was mixed with mCPBA (0.736 g, 4.75 mmol). The mixture was stirred at room temperature for about 10 minutes before directly loaded onto a column. Flash chromatography (mobile phase EtOAc/Hexane) then provided the title compound as a white solid 1.38 g (81%). MS (ES) m/z 538 (M+H)+; 1H-NMR (MeOD) δ 2.35 (s, 3 H), 2.81 (s, 3 H), 6.98 (d, J=10.0 Hz, 1 H), 7.30 (d, J=3.6 Hz, 1 H), 7.46 (t, J=8.6 Hz, 2 H), 7.57 (d, J=3.6 Hz, 1 H), 7.66 (d, J=8.0 Hz, 1 H), 7.72 (m, 1 H), 7.85 (d, J=10.0 Hz, 1 H), 8.25 (d, J=8.0 Hz, 2 H).

Sources & evidence

ORD record
ord-6977afd3f1d64f7dadb672132cc7f17c
Source dataset
uspto-grants-2013_01
Patent number
US08354416B2

Reaction notes

Loading…