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Trifluoroacetic acid → (3-(2-Fluoroethoxy)-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)(morpholino)methanone

HRID 2403479
Notes
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Reaction equation

HRID 2403479 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[CH:17][C:16]=1[O:29][CH2:30][CH2:31][F:32].FC(F)(F)C(O)=O>COCCO>[F:32][CH2:31][CH2:30][O:29][C:16]1[CH:17]=[C:18]([C:21]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[O:22])[CH:19]=[CH:20][C:15]=1[NH:14][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 210775872-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amineHCID 58539218(4-Amino-3-(2-fluoroethoxy)phenyl)(morpholino)methanone

Product 1

HCID 58539227(3-(2-Fluoroethoxy)-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)(morpholino)methanoneYield 29.3%

Reagents, catalysts & solvents 1

HCID 8019
2-Methoxyethanol
Solvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (0.10 g, 0.47 mmol), (4-amino-3-(2-fluoroethoxy)phenyl)(morpholino)methanone (0.13 g, 0.47 mmol), trifluoroacetic acid (0.07 mL, 0.9 mmol) in 2-methoxyethanol (2.5 mL) was stirred at 95° C. for 6 hours. The reaction was the concentrated. The crude product was purified by reverse phase HPLC to give the title compound (61 mg, 29%). Additional compounds made using the above procedure are shown in Table 6 below.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-6c5f170cae8a47c3928cb601f0c22017
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08802674B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes