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

HRID 1948934Notes

Reaction equation

HRID 1948934 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][C@@H:19]3[CH2:23][CH2:22][CH2:21][NH: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][C@@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[S:31]([CH3:30])(=[O:33])=[O:32])[CH:15]=2)[N:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 685223024-(3-chloro-2-fluoroanilino)-7-methoxy-6-[(2S)-pyrrolidin-2-ylmethoxy]quinazoline hydrochloride

Product 1

HCID 600366894-(3-Chloro-2-fluoroanilino)-7-methoxy-6-{[(2S)-1-methylsulfonylpyrrolidin-2-yl]methoxy}quinazolineYield 61%

Procedure

Using a similar procedure to that described in Example 29, 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[(2S)-pyrrolidin-2-yl]methoxy}quinazoline hydrochloride (300 mg) was reacted with methane sulfonyl chloride to give the title product (200 mg, 61%); 1H NMR Spectrum: (DMSO d6) 1.88-2.17 (m, 4H); 2.98 (s, 3H); 3.38 (m, 2H); 3.93 (s, 3H); 4.02 (m, 1H); 4.15 (m, 2H); 7.20 (s, 1H); 7.20-7.30 (m, 1H); 7.42-7.53 (m, 2H); 7.81 (s, 1H); 8.37 (s. 1H); 9.62 (s, 1H); Mass Spectrum: (M+H)+ 481.

Sources & evidence

ORD record
ord-22b62a68983f4581a7ca9475e9f3b502
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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