Potassium Carbonate → 4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(6-methylsulfanyl-pyridin-3-ylamino)pyrimidine-5-carbonitrile

HRID 1426078Notes

Reaction equation

HRID 1426078 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:12]=[N:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH:26]([C:29]1[N:33]=[C:32]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[O:31][N:30]=1)([CH3:28])[CH3:27].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH:26]([C:29]1[N:33]=[C:32]([CH:34]2[CH2:39][CH2:38][N:37]([C:2]3[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]4[CH:12]=[N:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=4)[N:5]=[CH:4][N:3]=3)[CH2:36][CH2:35]2)[O:31][N:30]=1)([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 534008274-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidine hydrochlorideHCID 859846374-Chloro-6-(6-methylsulfanyl-pyridin-3-ylamino)-pyrimidine-5-carbonitrile

Product 1

HCID 582164034-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(6-methylsulfanyl-pyridin-3-ylamino)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-6-(6-methylsulfanyl-pyridin-3-ylamino)-pyrimidine-5-carbonitrile (80.00 mg, 0.29 mmol) in DMF (2 ml) was mixture with Potassium Carbonate (79.62 mg, 0.58 mmol), added 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidine hydrochloride (237.4 mg, 1.08 or 1.02 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. Compound was recrystallized using hexane in ethyl acetate to afford Compound B136. 1H NMR 400 MHz DMSO δ (ppm): 9.48 (s,1H), 8.55 (d, 1H), 8.35 (s, 1H), 8.19 (s, 1H), 7.77 (d, 1H), 7.26 (d, 1H), 4.52(m, 2H), 3.48 (m, 1H), 3.37 (m, 2H), 3.32 (s, 3H), 3.04 (m, 1H), 2.14 (m, 2H), 1.75 (m, 2H), 1.33 (d, 6H).

Workup

  1. waitleft
  2. customReaction
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrate under high vacuum
  6. customCompound was recrystallized
  7. customto afford Compound B136

Sources & evidence

ORD record
ord-691b68ecc9f64d29ba4a37245909ae60
Source dataset
uspto-grants-2015_01
Patent number
US08933083B2

Reaction notes

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