4-((3-Chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-ol → HCID 68523549, compound

HRID 1948932Notes

Reaction equation

HRID 1948932 reaction equation
[Cl:1][C:2]1[C:3]([F:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[N:9]=[CH:8][N:7]=1.[N+](C1C=CC(S(O[C@@H:36]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37]2)(=O)=O)=CC=1)([O-])=O>>[Cl:1][C:2]1[C:3]([F:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([O:16][C@H:40]3[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:39]3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 574768684-((3-Chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-olHCID 86600825HCID 86600825, compound

Product 1

HCID 68523549HCID 68523549, compoundYield 95%

Procedure

4-(3-chloro-2-fluoroanilino)-6-hydroxy-7-methoxyquinazoline was reacted with tert-butyl (3R)-3-[(4-nitrophenyl)sulfonyloxy]pyrrolidine-1-carboxylate to give 4-(3-chloro-2-fluoroanilino)-6-[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy]-7-methoxyquinazoline as a dry foam (2.9 g, 95%); 1H NMR Spectrum: (DMSO d6) 1.40 (s, 9H); 2.07-2.29 (m, 21-1); 3.32-3.50 (m, 3H); 3.64-3.70 (dd, 1H); 3.92 (s, 3H); 5.08-5.18 (m, 1H); 7.21 (s, 1H); 7.23-7.30 (m, 1H); 7.43-7.55 (m, 2H); 7.79 (s, 1H); 8.36 (s, 1H); 9.6 (s, 1H); Mass Spectrum: (M+H)+ 489.

Sources & evidence

ORD record
ord-dc7fb8bc159843c1880f95c77aa1d14b
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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