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Water → 1-[4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(6-methanesulfonyl-pyridin-3-ylamino)-pyrimidin-5-yl]-ethanone

HRID 2067140
Notes
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Reaction equation

HRID 2067140 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([NH:11][C:12]2[CH:13]=[N:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][CH:17]=2)[N:5]=[CH:4][N:3]=1.Cl.[CH:23]([C:26]1[N:30]=[C:29]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[O:28][N:27]=1)([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:23]([C:26]1[N:30]=[C:29]([CH:31]2[CH2:36][CH2:35][N:34]([C:2]3[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([NH:11][C:12]4[CH:13]=[N:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][CH:17]=4)[N:5]=[CH:4][N:3]=3)[CH2:33][CH2:32]2)[O:28][N:27]=1)([CH3:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 534008274-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidine hydrochlorideHCID 865973601-[4-Chloro-6-(6-methanesulfonyl-pyridin-3-ylamino)-pyrimidin-5-yl]-ethanone

Product 1

HCID 582163651-[4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(6-methanesulfonyl-pyridin-3-ylamino)-pyrimidin-5-yl]-ethanone
Yield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[4-chloro-6-(6-methanesulfonyl-pyridin-3-ylamino)-pyrimidin-5-yl]-ethanone (0.21 mmol, 70 mg) and 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidine hydrochloride (0.21 mmol, 49 mg) in N,N-dimethyl formamide (500 uL) was added potassium carbonate (0.21 mmol, 29 mg). The mixture was microwaved at 100° C. for 150 seconds. Its progress was monitored by thin layer chromatography and LCMS. The reaction was treated with water and the desired compound was extracted in ethyl acetate. Organic layer was evaporated in vacuo. Purification by HPLC provided Compound B139 as a white solid (31 mg, 31%). 1H-NMR (400 MHz, CDCl3) δ(ppm): 10.9 (s, 1H); 8.90 (d, 1H); 8.58 (d, 1H); 8.32 (s, 1H); 8.05 (d, 1H); 4.09 (m, 2H); 3.41 (m, 2H); 3.29 (h, 1H); 3.23 (s, 3H); 3.09 (h, 1H); 2.48 (s, 3H), 2.18 (m, 2H), 2.02 (m, 2H), 1.35 (d, 6H) LCMS (ESI), m/z 486.3 (M+H+, 100%).

Workup

  1. customThe mixture was microwaved at 100° C. for 150 seconds
  2. extractionthe desired compound was extracted in ethyl acetate
  3. customOrganic layer was evaporated in vacuo
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-6edb4db337aa4e47a285406eedfea8e3
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293751B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes