Dimethylformamide → (S)-N-(1-(4-Bromophenyl)ethyl)-1H-pyrazole-4-carboxamide

HRID 40498

Reaction equation

HRID 40498 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[CH:3]=[N:2]1.CN(C=O)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Br:36][C:37]1[CH:42]=[CH:41][C:40]([C@@H:43]([NH2:45])[CH3:44])=[CH:39][CH:38]=1>>[Br:36][C:37]1[CH:42]=[CH:41][C:40]([C@@H:43]([NH:45][C:6]([C:4]2[CH:3]=[N:2][NH:1][CH:5]=2)=[O:8])[CH3:44])=[CH:39][CH:38]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3015937Pyrazole-4-carboxylic acid

Product 1

HCID 89672302(S)-N-(1-(4-Bromophenyl)ethyl)-1H-pyrazole-4-carboxamide

Procedure

To 5.0 g (44.6 mmol) 4-pyrazolecarboxylic acid in 100 mL DMF 15.2 mL (89.2 mmol) DIPEA and 15.7 g (49.1 mmol) TBTU are added and the mixture is stirred for 10 min at rt. Subsequently 8.9 g (44.6 mmol) (S)-1-(4-bromophenyl)ethylamine are added and stirring is continued over night. The mixture is poured on water and is extracted with ethyl acetate. The combined organic layers are dried over sodium sulphate and the solvent is removed in vacuo. The residue is triturated with DCM to yield the desired product.

Workup

  1. stirringstirring
  2. waitis continued over night
  3. additionThe mixture is poured on water
  4. extractionis extracted with ethyl acetate
  5. dry with materialThe combined organic layers are dried over sodium sulphate
  6. customthe solvent is removed in vacuo
  7. customThe residue is triturated with DCM

Sources & evidence

ORD record
ord-35c558e166d3439c925f4ad65b21b742
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Linked notes

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