Diisopropylethylamine → HCID 178520267, 화합물

HRID 1843603

반응식

HRID 1843603 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:3][CH:2]=1.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])(O)=O.[Na+]>ClCCl>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH:18][C:28](=[O:29])[CH2:27][C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:31])([F:19])[F:32])=[CH:26][CH:25]=4)[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:5][CH:6]=1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178507541HCID 178507541, 화합물

생성물 1

HCID 178520267HCID 178520267, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (80 mg, 0.339 mmol) (prepared as described in Example 6) in dichloromethane (8 mL), were added in the following order: (4-trifluoromethyl-phenyl)-acetic acid (138 mg, 0.678 mmol), DIPEA (131 mg, 174 uL, 1.017 mol) and TBTU (326 mg, 1.017 mol). The reaction mixture was stirred at room temperature for 4 hours. Then it was poured into a solution of saturated NaHCO3, the phases separated, and the organic phase was washed twice with saturated NaHCO3, and twice with water. The organic solvent was evaporated, and the residue taken up with methanol (5 mL). TEA (2 mL) was added, and the solution was stirred at room temperature overnight. After evaporation to dryness the compound was purified by flash chromatography, over silica gel, using dichloromethane-methanol (97:3) as the eluant system. N-[3-(4-Pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide was obtained as a colorless solid (125 mg, 87%).

후처리

  1. additionwere added in the following order
  2. customthe phases separated
  3. washthe organic phase was washed twice with saturated NaHCO3
  4. customThe organic solvent was evaporated
  5. additionTEA (2 mL) was added
  6. stirringthe solution was stirred at room temperature overnight
  7. customAfter evaporation to dryness the compound
  8. customwas purified by flash chromatography, over silica gel

출처 및 근거

ORD 기록
ord-cd67a341a4104992b7532f6d5f9bd236
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946250B2

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