Hydrochloric Acid → N-(3-chloro-4-fluorophenyl)-7-(cyclopropylmethoxy)-6-nitroquinazolin-4-amine

HRID 1582860Notes

Reaction equation

[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27](F)=[C:28]([N+:31]([O-:33])=[O:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH:16]=[CH:17][C:18]=1[F:19].Cl>CN(C)C=O.O>[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:5][CH2:4][CH:1]4[CH2:3][CH2:2]4)=[C:28]([N+:31]([O-:33])=[O:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

Conditions

Temperature: 10 °C

Procedure

29.36 g of cyclopropylmethanol are dissolved in 310 ml of N,N-dimethylformamide and cooled to about 10° C. in an ice bath. Then 41.58 g of potassium tert. butoxide are added batchwise, while the temperature should remain below 15° C. The reaction mixture is then stirred for another 30 minutes at 10° C., after which time 31.19 g of 4-[(3-chloro-4-fluoro-phenyl)amino]-7-fluoro-6-nitro-quinazoline are added batchwise, while again the temperature should not exceed 15° C. The deep red reaction mixture is stirred for another hour at 15° C. For working up, the mixture is poured onto 2.5 l of water and neutralised with 2N hydrochloric acid. The yellowish precipitate formed is suction filtered, washed with water and dried at 50° C. in a drying cupboard.

Workup

customshould remain below 15° C
customexceed 15° C
customThe deep red reaction mixture
stirringis stirred for another hour at 15° C
customThe yellowish precipitate formed
filtrationfiltered
washwashed with water
customdried at 50° C. in a drying cupboard

Sources & evidence

ORD record: ord-3796230834af4dd084466ab799f83b80
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740651B2

Reaction notes

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