Sodium Hydroxide → HCID 10521918, compound

HRID 1077553Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[NH:8][CH:9]=[CH:10][CH:11]=1)=O.[N+]([O-])(O)=O.[F:17][C:18]([F:33])([O:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]([NH2:32])=[NH:31])[CH:26]=[CH:27][CH:28]=1)[CH:19]([F:21])[F:20].[OH-].[Na+]>C(O)C(C)C>[F:17][C:18]([F:33])([O:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]2[N:32]=[C:5]([C:7]3[NH:8][CH:9]=[CH:10][CH:11]=3)[CH:4]=[CH:3][N:31]=2)[CH:26]=[CH:27][CH:28]=1)[CH:19]([F:20])[F:21]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 100 mg (0.61 mmol) of 3-dimethylamino-(1H-pyrrol-2-yl)2-propen-1-one [described in EP-A-0 233 461]in 4 ml of isobutanol are added 185 mg (0.60 mmol) of 3-(1,1,2,2-tetrafluoroethoxy)phenylguanidine nitrate. Following the addition of 32.5 mg (0.81 mmol) of sodium hydroxide, the reaction mixture is stirred for 3 hours at 110° C. The suspension is concentrated under reduced pressure, the residue is dissolved in 4 ml of methylene chloride/tetrahydrofuran (1:1 ), and the solution is extracted with 2.4 ml of water. The organic phase is dried over sodium sulfate and concentrated on a rotovap. Recrystallisation from diethyl ether/tetrahydrofuran gives N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-(1H-pyrrol-2-yl)-2-pyrimidine-amine; FAB-MS:353 (M+ +1 ), m.p. 142-143, Rf =0.83 (methylene chloride:methanol=9:1).

Workup

concentrationThe suspension is concentrated under reduced pressure
dissolutionthe residue is dissolved in 4 ml of methylene chloride/tetrahydrofuran (1:1 )
extractionthe solution is extracted with 2.4 ml of water
dry with materialThe organic phase is dried over sodium sulfate
concentrationconcentrated on a rotovap
customRecrystallisation from diethyl ether/tetrahydrofuran

Sources & evidence

ORD record: ord-36075aa905004ad8a0e840f542e5ac57
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05543520

Reaction notes

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