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

HRID 40498노트

반응식

HRID 40498 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-35c558e166d3439c925f4ad65b21b742
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530461B2

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