HCID 58345904, 화합물 → HCID 58553169, 화합물

HRID 1046528

반응식

HRID 1046528 반응식
CS([C:4]1[N:9]=[C:8]([C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:22])([CH3:21])[CH3:20])[C:13]3=[N:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1)=O.[CH3:23][S:24]([CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)(=[O:26])=[O:25]>CN1C(=O)CCC1.O>[CH3:23][S:24]([CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([NH:34][C:4]2[N:9]=[C:8]([C:10]3[N:14]4[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:22])([CH3:20])[CH3:21])[C:13]4=[N:12][CH:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:30][CH2:29]1)(=[O:25])=[O:26]

참가 물질

5

반응물 2

HCID 58345904HCID 58345904, 화합물HCID 666162852-[3-(2-Methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol

생성물 1

HCID 58553169HCID 58553169, 화합물수율 52.8%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-[3-(2-methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol (75 mg), 4-methanesulfonylmethyl-cyclohexylamine (162 mg), and TEA (0.165 mL) in NMP (2 mL) was stirred at 100° C. overnight. The reaction mixture was then cooled to RT, and diluted with water. The resulting precipitate was filtered and dried, then purified by ISCO using 100% DCM to 10% MeOH/DCM. The fractions were collected, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide 2-{3-[2-(4-methanesulfonylmethyl-cyclohexylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyridin-8-yl}-propan-2-ol (Compound 1, 55.5 mg). Mp=223-224° C.

후처리

  1. temperatureThe reaction mixture was then cooled to RT
  2. filtrationThe resulting precipitate was filtered
  3. customdried
  4. custompurified by ISCO
  5. customThe fractions were collected
  6. concentrationconcentrated
  7. filtrationThe resulting solid was filtered
  8. customdried at 50° C. under vacuum overnight

출처 및 근거

ORD 기록
ord-8172da2e90f4453281532ffa792a72a2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569306B2

연결된 노트

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