Dimethylformamide → HCID 58216546, compound

HRID 1426077Notes

Reaction equation

HRID 1426077 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=C[CH:12]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32](=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+].C[N:45](C=O)C>C(OCC)(=O)C>[C:32]([CH:29]1[CH2:30][CH2:31][N:26]([C:2]2[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]3[CH:12]=[N:45][C:14]([S:17][CH3:18])=[CH:15][CH:16]=3)[N:5]=[CH:4][N:3]=2)[CH2:27][CH2:28]1)(=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 67117494HCID 67117494, compoundHCID 85984633HCID 85984633, compound

Product 1

HCID 58216546HCID 58216546, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-6-(4-methylsulfanyl-phenylamino)-pyrimidine-5-carbonitrile (150.00 mg, 0.54 mmol) in DMF (2 ml) was mixture with Potassium Carbonate (82.1 mg, 0.59 mmol), added 1-piperidin-4-yl-hexan-1-one hydrochloride (237.4 mg, 1.08 mmol) in DMF (1 ml) and left stirring at room temperature for 1 hour. Reaction was worked up with ethyl acetate, sodium bicarbonate, dried with magnesium sulfate, filtered and concentrate under high vacuum to afford a lithe yellow solid as product. Compound was recrystallized using hexane in ethyl acetate to afford Compound B134 (157 mg). LCMS (ESI) for C22H28N6OS: m/z 425.4 (M+H+, 100%). 1H NMR 400 MHz CDCl3 δ (ppm): 8.72 (d, 1H), 8.40 (s, 1H), 7.97 (q, 1H), 7.21 (s,1H,NH), 4.92 (m, 2H), 3.42 (m, 2H), 2.86 (m, 1H), 2.75 (s, 3H), 2.65 (t, 2H), 2.15 (m, 2H), 1.77 (m, 2H), 1.50(m, 2H), 1.50 (m, 2H), 1.07 (t, 3H).

Workup

  1. waitleft
  2. customReaction
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrate under high vacuum
  6. customto afford a lithe yellow solid as product
  7. customCompound was recrystallized
  8. customto afford Compound B134 (157 mg)

Sources & evidence

ORD record
ord-270bbe5d65074fe18236ddd2085f4aec
Source dataset
uspto-grants-2015_01
Patent number
US08933083B2

Reaction notes

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