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

HRID 1631180Notes

Reaction equation

HRID 1631180 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[CH2:31]O)[CH:8]=2)[N:3]=1.S(Cl)([Cl:35])=O>>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[CH2:31][Cl:35])[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 56943446[2-Amino-6-[4,5-difluoro-2-(hydroxymethyl)phenyl]quinazolin-4-yl]isoindolin-2-ylmethanone

Product 1

HCID 66837605[2-Amino-6-(2-chloromethyl-4,5-difluorophenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone

Conditions

Temperature
25 °C

Procedure

50 ml of thionyl chloride are added to 2 g of [2-amino-6-(4,5-difluoro-2-hydroxymethylphenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone, and the mixture is stirred at 25° C. for 1 h. The mixture is subsequently evaporated to dryness in vacuo, the residue is taken up a further twice with 50 ml of dichloromethane each time, and the mixture is again evaporated to dryness in vacuo.

Workup

  1. customThe mixture is subsequently evaporated to dryness in vacuo
  2. customthe mixture is again evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5eba8f0074564f529e7bca88b8392a03
Source dataset
uspto-grants-2014_07
Patent number
US08791129B2

Reaction notes

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