Potassium Phosphate, Tribasic → 5-Cyclopropyl-2-(2-(2-cyclopropylphenyl)pyrimidin-5-ylamino)benzoic acid

HRID 42062

반응식

HRID 42062 반응식
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:26][CH2:25]3)=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=[CH:10][N:9]=1.[CH:27]1(B(O)O)[CH2:29][CH2:28]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.O>[CH:24]1([C:21]2[CH:22]=[CH:23][C:15]([NH:14][C:11]3[CH:10]=[N:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH:27]4[CH2:29][CH2:28]4)=[N:13][CH:12]=3)=[C:16]([CH:20]=2)[C:17]([OH:19])=[O:18])[CH2:26][CH2:25]1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 569684702-(2-(2-Chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid

생성물 1

HCID 251867195-Cyclopropyl-2-(2-(2-cyclopropylphenyl)pyrimidin-5-ylamino)benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 22272177Toluene water용매

반응 조건

온도
110 °C

실험 절차

In a schlenck tube, a mixture of 2-(2-(2-chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid (0.55 mmol, 0.200 g), cyclopropylboronic acid (0.71 mmol, 0.061 g), K3PO4 (1.86 mmol, 0.395 g), PCy3 (0.05 mmol, 0.015 g) and Pd(AcO)2 (0.03 mmol, 0.006 g) in a mixture of toluene/water 6:1 (6 ml) was heated at 110° C. for 72 hours, under argon atmosphere. The crude mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and the solvent removed. The crude mixture was purified by reverse phase chromatography eluting with a gradient of 100% water to 100% MeOH/AcN 1:1 affording 0.016 g (71% of yield).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed
  5. customThe crude mixture was purified by reverse phase chromatography
  6. washeluting with a gradient of 100% water to 100% MeOH/AcN 1:1 affording 0.016 g (71% of yield)

출처 및 근거

ORD 기록
ord-b5c7b4767f8d4872b12910c4e9cdaa0a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536165B2

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