Acetic Anhydride → HCID 68522238, compound

HRID 1948947Notes

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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 68521248HCID 68521248, compound

Product 1

HCID 68522238HCID 68522238, compoundYield 66%

Procedure

Using a procedure similar to that described in Example 38, 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-[(2R)-pyrrolidin-2-ylmethoxy]quinazoline hydrochloride (300 mg; prepared as described in Example 32-preparation of starting materials) was reacted with acetic anhydride to give the title product (203 mg, 66%); 1H NMR Spectrum (DMSO d6) 1.89-2.05 (m, 6H); 2.11-2.21 (m, 1H); 3.43-3.56 (m, 2H); 3.94 (s, 3H); 4.00-4.11 (m, 1H); 4.17-4.21 (m, 1H); 4.30-4.37 (m, 1H); 7.19-7.29 (m, 2H); 7.42-7.53 (m, 2H); 7.79-7.82 (m, 1H); 8.37 (s, 1H); 9.54-9.57 (m, 1H); Mass Spectrum (M+H)# 445.

Sources & evidence

ORD record: ord-c725baee8584470c982164624dd5c097
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399667B2

Reaction notes

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