Methanesulfonyl chloride → 4-(3-Chloro-2-fluoroanilino)-7-methoxy-6-{[1-(methylsulfonyl)pyrrolidin-3-yl]methoxy}quinazoline

HRID 1948938Notes

Reaction equation

HRID 1948938 reaction equation
Cl.[Cl:2][C:3]1[C:4]([F:29])=[C:5]([CH:26]=[CH:27][CH:28]=1)[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:24][CH3:25])=[C:14]([O:17][CH2:18][CH:19]3[CH2:23][CH2:22][NH:21][CH2:20]3)[CH:15]=2)[N:10]=[CH:9][N:8]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>>[Cl:2][C:3]1[C:4]([F:29])=[C:5]([CH:26]=[CH:27][CH:28]=1)[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:24][CH3:25])=[C:14]([O:17][CH2:18][CH:19]3[CH2:23][CH2:22][N:21]([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:20]3)[CH:15]=2)[N:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68519314HCID 68519314, compound

Product 1

HCID 104803234-(3-Chloro-2-fluoroanilino)-7-methoxy-6-{[1-(methylsulfonyl)pyrrolidin-3-yl]methoxy}quinazolineYield 67%

Procedure

Using a similar procedure to that described in Example 29, 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-(pyrrolidin-3-ylmethoxy)quinazoline hydrochloride (300 mg) was reacted with methane sulfonyl chloride to give the title product (200 mg, 67%); 1H-NMR Spectrum: (DMSO d6+CD3COOD) 1.75-1.89 (m, 1H); 2.08-2.18 (m, 1H); 2.77-2.86 (m, 1H); 2.91 (s, 3H); 3.12-3.18 (m, 1H); 3.25-3.43 (m, 2H); 3.47-3.52 (m, 1H); 3.94 (s, 3H; 4.06-4.09 (m, 2H); 7.15-7.30 (m, 2H); 7.43-7.53 (m, 2H): 7.81 (s, 1H); 8.38 (s, 1H); Mass Spectrum: (M+H)+ 481.

Sources & evidence

ORD record
ord-c76310538f134ebc8cb4fd9068a8d92d
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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