N-(4-aminocyclohexyl)methanesulfonamide → N-(4-{4-[8-(1-hydroxy-1-methyl-ethyl)-imidazo[1,2-a]pyridine-3-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanesulfonamide

HRID 1046532

반응식

HRID 1046532 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.[NH2:23][CH:24]1[CH2:29][CH2:28][CH:27]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH2:26][CH2:25]1>CN1C(=O)CCC1.O>[OH:22][C:19]([C:18]1[C:13]2[N:14]([C:10]([C:8]3[CH:7]=[CH:6][N:5]=[C:4]([NH:23][CH:24]4[CH2:29][CH2:28][CH:27]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH2:26][CH2:25]4)[N:9]=3)=[CH:11][N:12]=2)[CH:15]=[CH:16][CH:17]=1)([CH3:20])[CH3:21]

참가 물질

5

반응물 2

HCID 18348422N-(4-aminocyclohexyl)methanesulfonamideHCID 666162852-[3-(2-Methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol

생성물 1

HCID 46896571N-(4-{4-[8-(1-hydroxy-1-methyl-ethyl)-imidazo[1,2-a]pyridine-3-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanesulfonamide수율 40.3%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
105 °C

실험 절차

A mixture of 2-[3-(2-methanesulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridine-8-yl]-propan-2-ol (0.15 g) and N-(4-amino-cyclohexyl)-methanesulfonamide (0.325 g) in NMP (1.5 mL) was treated with TEA (0.33 mL) and heated at 105° C. for 18 h. The reaction mixture was then cooled to RT and diluted with water. The resulting precipitate was filtered, washed with water, and dried. The product was purified by ISCO using 100% DCM to 15% MeOH/DCM. Pure fractions were collected, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide N-(4-{4-[8-(1-hydroxy-1-methyl-ethyl)-imidazo[1,2-a]pyridine-3-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanesulfonamide (compound 3, 84.9 mg).

후처리

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

출처 및 근거

ORD 기록
ord-ff4c82885dc34545a3e02abac5381f64
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569306B2

연결된 노트

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