Triethylamine → 1-(5-tert-Butyl-isoxazol-3-yl)-3-(4-{7-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-urea

HRID 1446752노트

반응식

HRID 1446752 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][N:17]4[C:20]([C:23]5[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=5)=[CH:21][N:22]=[C:16]4[CH:15]=3)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.ClC(Cl)(Cl)C[O:33][C:34](=O)[NH:35][C:36]1[CH:40]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[O:38][N:37]=1.C(N(CC)CC)C>CS(C)=O>[C:41]([C:39]1[O:38][N:37]=[C:36]([NH:35][C:34]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([C:20]3[N:17]4[CH:18]=[CH:19][C:14]([C:11]5[CH:12]=[N:13][C:8]([N:5]6[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]6)=[N:9][CH:10]=5)=[CH:15][C:16]4=[N:22][CH:21]=3)=[CH:24][CH:25]=2)=[O:33])[CH:40]=1)([CH3:44])([CH3:42])[CH3:43]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 22768171HCID 22768171, 화합물HCID 685432324-{7-[2-(4-Methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenylamine

생성물 1

HCID 578634401-(5-tert-Butyl-isoxazol-3-yl)-3-(4-{7-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-urea

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
70 °C

실험 절차

Combine the amine (0.323 g, 0.838 mmol), (5-tert-butyl-isoxazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (0.291 g, 0.922 mmol) and triethylamine (0.128 mL, 0.922 mmol) in DMSO (10 mL). Heat the mixture to 70° C., stir overnight, and cool to room temperature. Extract the mixture with ethyl acetate versus water. Wash the organic layer with saturated aqueous saturated sodium chloride. Dry the resulting organics over magnesium sulfate, filter, and concentrate. Purify by column chromatography (ethyl acetate→10% methanol in dichloromethane→10% 2 M NH3 in MeOH in dichloromethane) to afford product (0.057 g, 11%, two steps). MS(ES), m/z 552 (M+1).

후처리

  1. temperaturecool to room temperature
  2. extractionExtract the mixture with ethyl acetate versus water
  3. washWash the organic layer with saturated aqueous saturated sodium chloride
  4. dry with materialDry the resulting organics over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by column chromatography (ethyl acetate→10% methanol in dichloromethane→10% 2 M NH3 in MeOH in dichloromethane)
  8. customto afford product (0.057 g, 11%, two steps)

출처 및 근거

ORD 기록
ord-1b5b4bcb03c1466d95010c85d4705b23
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666879B2

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