Dimethylamine → 4-(3-Chloro-2-fluoroanilino)-7-methoxy-6-{[(2S)-1-(N,N-dimethylaminoacetyl) pyrrolidin-2-yl]methoxy}quinazoline

HRID 1948964Notes

Reaction equation

HRID 1948964 reaction equation
[Cl:1][C:2]1[C:3]([F:32])=[C:4]([CH:29]=[CH:30][CH:31]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:16][CH2:17][C@@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[C:23](=[O:26])[CH2:24]Cl)[CH:14]=2)[N:9]=[CH:8][N:7]=1.[CH3:33][NH:34][CH3:35]>C(O)C>[Cl:1][C:2]1[C:3]([F:32])=[C:4]([CH:29]=[CH:30][CH:31]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:16][CH2:17][C@@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[C:23](=[O:26])[CH2:24][N:34]([CH3:35])[CH3:33])[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 685201434-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[(2S)-1-(chloroacetyl)pyrrolidin-2-yl]methoxy}quinazoline

Product 1

HCID 104581894-(3-Chloro-2-fluoroanilino)-7-methoxy-6-{[(2S)-1-(N,N-dimethylaminoacetyl) pyrrolidin-2-yl]methoxy}quinazolineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using a procedure similar to that described for the preparation of Example 43, 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[(2S)-1-(chloroacetyl)pyrrolidin-2-yl]methoxy}quinazoline (0.28 g) was reacted with 33% dimethylamine in ethanol (5 ml) to give the title product as a foam (0.165 g, 58%); 1H NMR Spectrum: (CDCl3) 1.91-2.01 (m, 1H), 2.04-2.11 (m, 2H), 2.14-2.22 (m, 1H), 2.33 (s, 6H), 3.02-3.22 (dd, 2H), 3.40-3.50 (m, 1H), 3.59-3.66 (m, 1H), 4.02 (s, 3H), 4.05-4.09 (m, 1H), 4.51-4.55 (d, 1H), 4.66-4.72 (m, 1H), 7.09-7.21 (m, 2H), 7.23 (s, 1H), 8.00-8.06 (m, 1H), 8.47 (bs, 1H), 8.62 (s, 1H), 8.68 (s, 1H); Mass Spectrum: (M−H)− 486.

Sources & evidence

ORD record
ord-165fefe3dc7f4183a17bf6f4c5593b7f
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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