N-bromobutanimide → HCID 86658556, compound

HRID 1520201Notes

Reaction equation

HRID 1520201 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:16][CH:17]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[Br:27]N1C(=O)CCC1=O>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:16][C:17]=3[Br:27])[CH:10]=[N:9]2)=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 86642330N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-2-amine

Product 1

HCID 86658556HCID 86658556, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

According to Scheme 5 Step 1: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-2-amine (4.20 mmol, 1.53 g) and N-bromosuccinimide (4.40 mmol, 782 mg) in DMF (76 mL) was stirred for 1.5 hour at 50° C. The reaction mixture was diluted with a saturated solution of Na2CO3 and water. The precipitate formed was recovered and washed with DCM. The aqueous phase was extracted with DCM and the organic phase was washed. The organic phase was dried over MgSO4, was filtered and was concentrated to yield with the addition of the precipitate N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-bromothiazol-2-yl)pyridin-2-amine (4.02 mmol, 1.78 g, 96%) as a beige solid.

Workup

  1. customThe precipitate formed
  2. customwas recovered
  3. washwashed with DCM
  4. extractionThe aqueous phase was extracted with DCM
  5. washthe organic phase was washed
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationwas filtered
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-aab2c10129b44404856c0bcb318415f5
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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