Trifluoroacetic acid → HCID 71577883, compound

HRID 2283515Notes

Reaction equation

HRID 2283515 reaction equation
[NH2:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:12])[CH:3]=1.Cl[C:14]1[N:19]=[C:18]([NH:20][CH3:21])[C:17]([C:22]([F:25])([F:24])[F:23])=[CH:16][N:15]=1.C(O)(C(F)(F)F)=O>C(O)CCC>[F:12][C:4]1[CH:3]=[C:2]([NH:1][C:14]2[N:19]=[C:18]([NH:20][CH3:21])[C:17]([C:22]([F:25])([F:23])[F:24])=[CH:16][N:15]=2)[C:9]([O:10][CH3:11])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 210775872-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amineHCID 71743885HCID 71743885, compound

Product 1

HCID 71577883HCID 71577883, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 4-amino-2-fluoro-5-methoxybenzonitrile (66 mg, 0.40 mmol) and 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (0.10 g, 0.47 mmol) in 1-butanol (2 mL) was added TFA (0.05 mL, 0.07 mmol). The reaction was stirred in a sealed tube at 75° C. for 2 h. The reaction was concentrated and the product was isolated by reverse-phase HPLC to give 2-fluoro-5-methoxy-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzonitrile. 1H NMR (400 MHz, DMSO) δ 8.57 (d, J=13.4, 2H), 8.34 (s, 1H), 8.29 (d, J=6.1, 1H), 7.56-7.42 (m, 3H), 3.93 (s, 3H), 2.95 (s, 3H); LRRK2 Ki=0.022.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe product was isolated by reverse-phase HPLC

Sources & evidence

ORD record
ord-03be29d22fe1405083e2e27f38e6dbc6
Source dataset
uspto-grants-2015_09
Patent number
US09145402B2

Reaction notes

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