Potassium Phosphate, Dibasic → N-(3-((2-(4-(1-hydroxyethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)-N-methylmethanesulfonamide

HRID 886999

반응식

HRID 886999 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[C:11]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[N:12][CH:13]=[CH:14][CH:15]=2)[C:5]([C:22]([F:25])([F:24])[F:23])=[CH:4][N:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]([OH:35])[CH3:34])=[CH:29][CH:28]=1.OP([O-])([O-])=O.[K+].[K+]>CS(C)=O>[OH:35][CH:33]([C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:2]2[N:7]=[C:6]([NH:8][CH2:9][C:10]3[C:11]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[N:12][CH:13]=[CH:14][CH:15]=3)[C:5]([C:22]([F:25])([F:24])[F:23])=[CH:4][N:3]=2)=[CH:28][CH:29]=1)[CH3:34]

참가 물질

5

반응물 3

HCID 24450Potassium Phosphate, DibasicHCID 857534-Amino-alpha-methylbenzenemethanol2회HCID 57584561N-(3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)-N-methylmethanesulfonamide

생성물 1

HCID 25117123N-(3-((2-(4-(1-hydroxyethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)-N-methylmethanesulfonamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
100 °C

실험 절차

A solution of C9 (0.253 mmol) and anhydrous DMSO (0.5 ml) was treated with 1-(4-aminophenyl)ethanol (0.277 mmol) followed by potassium phosphate dibasic (0.746 mmol). The mixture was stirred at 100° C. for 1.5 days, and treated with additional 1-(4-aminophenyl)ethanol (0.583 mmol). The mixture was stirred at 100° C. for 15 hours and concentrated. The resultant residue was purified first by column chromatography (silica gel; 10% (NH4OH/MeOH)/CH2Cl2) followed by preparatory thin layer chromatography developed in 5% MeOH/CH2Cl2 to provide 12. Yield: 13.6 mg, 10.8%. 1H NMR(CD3OD) δ: 8.39(d, 1H), 8.13(s, 1H), 7.73(d, 1H), 7.33(m, 3H), 7.14(d, 2H), 4.87(s, 2H), 4.72(q, 1H), 3.17(s, 3H), 3.10(s, 3H), 1.37(d, 3H). MS: m/z 497(MH+).

후처리

  1. stirringThe mixture was stirred at 100° C. for 15 hours
  2. concentrationconcentrated
  3. customThe resultant residue was purified first by column chromatography (silica gel; 10% (NH4OH/MeOH)/CH2Cl2)

출처 및 근거

ORD 기록
ord-afd9d24d1b2844358d5fc8320024564d
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247411B2

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