Water → N-(3-ethynyl-4-fluorophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine

HRID 712410Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:22][CH3:23])=[C:18]([OH:21])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[F:9])#[CH:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:31][CH2:32][CH2:33][Cl:34].O>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:22][CH3:23])=[C:18]([O:21][CH2:31][CH2:32][CH2:33][Cl:34])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[F:9])#[CH:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 4-((3-ethynyl-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (3.90 g), K2CO3 (4.36 g) in DMF (30 mL) was added 1-bromo-3-chloropropane (3.80 mL) at rt, the mixture was stirred at 40° C. overnight. The reaction mixture was poured into water and filtered. The filter residue was purified by a silica gel column chromatography (eluting agent: 3:1 (v/v) PE/EA) to give the title compound as a white solid (3.30 g, 68.00%).

Workup

filtrationfiltered
customThe filter residue was purified by a silica gel column chromatography (eluting agent: 3:1 (v/v) PE/EA)

Sources & evidence

ORD record: ord-9f1c9226a2704ffb9626b6ae3c8a63d1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181277B2

Reaction notes

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