3-Chloro-2-fluoroaniline → HCID 68521248, compound

HRID 1948937Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:26][CH3:27])=[C:9]([O:12][CH2:13][C@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3C(OC(C)(C)C)=O)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:28][C:29]1[C:30]([F:36])=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32]>>[ClH:1].[Cl:28][C:29]1[C:30]([F:36])=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH:32][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:26][CH3:27])=[C:9]([O:12][CH2:13][C@H:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 750143-Chloro-2-fluoroaniline

HCID 86600827HCID 86600827, compound

Product 1

HCID 68521248HCID 68521248, compoundYield 100%

Procedure

4-chloro-7-methoxy-6-{[(2R)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methoxy}quinazoline was reacted with 3-chloro-2-fluoroaniline to give 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[(2R)-pyrrolidin-2-yl]methoxy}quinazoline hydrochloride (5.3 g 100%); 1H NMR Spectrum: (DMSO d6) 1.70-1.84 (m, 1H); 1.87-1.97 (m, 1H); 1.99-2.08 (m, 1H); 2.17-2.28 (m, 1H); 3.18-3.27 (m, 2H); 3.98-4.10 (m, 4H); 4.45-4.57 (m, 2H); 7.32-7.38 (m, 1H); 7.47 (s, 1H); 7.49-7.55 (m, 1H); 7.59-7.65 (m, 1H); 8.66 (s, 1H); 8.81 (s, 1H); 9.30 (bs, 1H); 9.67 (bs, 1H); 12.09 (bs, 1H); Mass Spectrum: (M−H)− 401.

Sources & evidence

ORD record: ord-8891d8c1b8f0428c9be1c6c7c5f11ecc
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399667B2

Reaction notes

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