Water → 5-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamide

HRID 643037

반응식

HRID 643037 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[I:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[N:18]2)=[CH:13][CH:12]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:23][CH2:22][C:19]2[CH:20]=[CH:21][N:17]([C:14]3[CH:15]=[CH:16][C:11]([I:10])=[CH:12][CH:13]=3)[N:18]=2)=[O:9])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 65805535(1-(4-iodophenyl)-1H-pyrazol-3-yl)methanamine

생성물 1

HCID 685066795-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamide수율 52%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-chloro-thiophene-2-carboxylic acid (51 mg, 0.31 mmol), (1-(4-iodophenyl)-1H-pyrazol-3-yl)methanamine (78 mg, 0.26 mmol) and TEA (0.100 mL, 0.72 mmol) in DMF (3 mL), BOP (170 mg, 0.38 mmol) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by a preparative TLC plate (developed in EtOAc/hexane (35/65)) to give 5-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamide (60 mg).

후처리

  1. customThe organic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a preparative TLC plate (developed in EtOAc/hexane (35/65))

출처 및 근거

ORD 기록
ord-1125d96caeaa45fd951da7eb6945a31e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696352B2

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