Trifluoroacetic acid → HCID 58709979, compound

HRID 2375890Notes

Reaction equation

HRID 2375890 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:24]1([NH2:34])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>FC(F)(F)CO>[C:24]1([NH:34][C:21]2[C:16]3[CH:15]=[C:14]([C:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH:12]=4)[NH:23][C:17]=3[N:18]=[CH:19][N:20]=2)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 86401-NaphthylamineHCID 516892Sodium BicarbonateHCID 58709797tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 58709979HCID 58709979, compound

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Conditions

Temperature
80 °C

Procedure

A sealed tube containing a solution of 4-(4-chloro-7H-pyrrolo[2,3-d]-pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (250 mg, 0.75 mmol), 1-naphthylamine (160 mg, 1.12 mmol) and trifluoroacetic acid (287 μL, 3.73 mmol) in 2,2,2-trifluoroethanol (5 mL) was heated at 80° C. and maintained at this temperature overnight. The product was poured into saturated NaHCO3 solution (50 mL) and the precipitate was filtered off, giving the title compound as an off-white solid. 1H NMR (DMSO-d6, 400 MHz): δ=9.48 (1H, s), 8.14-7.92 (3H, m), 7.82 (1H, d, J=8.0 Hz), 7.64 (1H, d, J=7.2 Hz), 7.61-7.44 (3H, m), 6.40 (1H, s), 4.02 (2H, brs), 3.51 (2H, brs), 2.89 (2H, brs); MS (ES+): m/z 342.11 [MH+], HPLC: tR=1.71 min (MicromassZQ, polar—5 min).

Workup

  1. temperaturemaintained at this temperature overnight
  2. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-7c10dc4382594a2eaf1f55d1c108514e
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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