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Thionyl Chloride → [2-Amino-6-(2-chloromethyl-5-fluorophenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone

HRID 1631159
Notes
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Reaction equation

HRID 1631159 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[N:15]=[C:14]([C:16]([N:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[CH2:34]O)[CH:12]=2)[N:7]=1>ClCCl>[NH2:5][C:6]1[N:15]=[C:14]([C:16]([N:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[CH2:34][Cl:3])[CH:12]=2)[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 56943415[2-Amino-6-[5-fluoro-2-(hydroxymethyl)phenyl]quinazolin-4-yl]isoindolin-2-ylmethanone

Product 1

HCID 66837686[2-Amino-6-(2-chloromethyl-5-fluorophenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

218 μl of thionyl chloride are added dropwise to 622 mg of [2-amino-6-(2-hydroxymethyl-5-fluorophenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone in 50 ml of dichloromethane, and the mixture is stirred at 25° C. for 2 h. The mixture is evaporated to dryness in vacuo, the residue is taken up in 10 ml of toluene, and the operation is repeated. The residue is employed in the subsequent reactions without further treatment.

Workup

  1. customThe mixture is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-dd4344220068427989e255daebe52c94
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791129B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes