Thionyl Chloride → 6-(1-chloroethyl)-N-(3-chloro-2-fluorophenyl)-7-methoxyquinazolin-4-amine hydrochloride

HRID 1867761Notes

Reaction equation

HRID 1867761 reaction equation
[Cl:1][C:2]1[C:3]([F:24])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH3:23])=[C:16]([CH:19](O)[CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:27])=O>>[ClH:1].[Cl:27][CH:19]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:22][CH3:23])[N:12]=[CH:11][N:10]=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:24])[CH3:20]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 579798031-{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}ethanol

Product 1

HCID 690475966-(1-chloroethyl)-N-(3-chloro-2-fluorophenyl)-7-methoxyquinazolin-4-amine hydrochloride

Procedure

1-{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}ethanol was reacted with thionyl chloride using an analogous procedure to that described for the equivalent step in Example 62 to give 6-(1-chloroethyl)-N-(3-chloro-2-fluorophenyl)-7-methoxyquinazolin-4-amine hydrochloride; 1H NMR Spectrum: (DMSO d6) 1.97 (d, 3H); 4.07 (s, 3H); 5.66 (q, 1H); 7.37 (m, 2H); 7.56 (m, 1H); 7.65 (m, 1H); 8.87 (s, 1H); 9.04 (s, 1H).

Sources & evidence

ORD record
ord-427ee0d1ff5c4933b790d0a56b4ecaee
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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