Acetic Anhydride → 6-[(1-Acetylpyrrolidin-3-yl)methoxy]-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline

HRID 1948948Notes

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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 68519314HCID 68519314, compound

Product 1

HCID 117442016-[(1-Acetylpyrrolidin-3-yl)methoxy]-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolineYield 63%

Procedure

Using a procedure similar to that described in Example 38, 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-(pyrrolidin-3-ylmethoxy)quinazoline hydrochloride (300 mg; prepared as described in Example 33-starting material) was reacted with acetic anhydride to give the title product (194 mg, 63%); 1H NMR Spectrum (DMSO d6+CD3COOD) 1.71-1.90 (m, 1H); 1.93-1.94 (m, 3H); 2.00-2.20 (m, 1H); 2.66-2.86 (m, 1H); 3.18-3.31 (m, 1H); 3.43-3.72 (m, 3H); 3.93 (m, 3H); 4.04-4.18 (m, 2H); 7.15-7.32 (m, 2H); 7.42-7.53 (m, 2H); 7.78-7.80 (m, 1H); 8.35-8.37 (m, 1H); Mass Spectrum: (M+H)+ 445.

Sources & evidence

ORD record: ord-b0a14f1f60a74e879f3c14765bbb7b72
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399667B2

Reaction notes

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