Water → HCID 58216365, compound

HRID 1426079Notes

Reaction equation

HRID 1426079 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]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 534008274-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidine hydrochlorideHCID 86597360HCID 86597360, compound

Product 1

HCID 58216365HCID 58216365, compoundYield 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-11a2b6fbf2ef4827bf3e79374b41228a
Source dataset
uspto-grants-2015_01
Patent number
US08933083B2

Reaction notes

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