Piperidine → N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(piperidin-1-yl)thiazol-2-yl)pyridin-2-amine

HRID 1520202Notes

Reaction equation

HRID 1520202 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[S:16][C:17]=3Br)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[S:16][C:17]=3[N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 86658556HCID 86658556, compound

Product 1

HCID 86658557N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(piperidin-1-yl)thiazol-2-yl)pyridin-2-amineYield 26.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to Scheme 5 Step 2: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-bromothiazol-2-yl)pyridin-2-amine (2.16 mmol, 1.00 g), piperidine (8.64 mmol, 0.89 mL) and Et3N (12.9 mmol, 1.81 mL) in DMF (10 mL) was microwaved for 30 minutes at 150° C. The reaction mixture was diluted with AcOEt and water. The aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4, was filtered and was concentrated to yield N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(piperidin-1-yl)thiazol-2-yl)pyridin-2-amine (0.58 mmol, 263 mg, 26%) as a beige solid.

Workup

  1. extractionThe aqueous phase was extracted with AcOEt
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationwas filtered
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-84d4bfcd3eb549028eb1c63e5f251df1
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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