Diisopropylethylamine → N-[4-(5-fluoro-4-indol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide

HRID 1947037노트

반응식

HRID 1947037 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[C:5]([F:17])=[CH:4][N:3]=1.[NH2:18][CH:19]1[CH2:24][CH2:23][CH:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:21][CH2:20]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.C(Cl)Cl>[F:17][C:5]1[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[N:7][C:2]([NH:18][CH:19]2[CH2:24][CH2:23][CH:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:21][CH2:20]2)=[N:3][CH:4]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 18348422N-(4-aminocyclohexyl)methanesulfonamideHCID 866208441-(2-chloro-5-fluoro-pyrimidin-4-yl)-1H-indole

생성물 1

HCID 59743430N-[4-(5-fluoro-4-indol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

1-(2-Chloro-5-fluoro-pyrimidin-4-yl)-1H-indole (0.095 g, 0.38 mmol), N-(4-amino-cyclohexyl)-methanesulfonamide (0.17 g, 0.76 mmol), and DIEA (0.13 mL, 0.76 mmol) were stirred in NMP (2 mL) at 170° C. for 4.5 hours. The solvent was removed at 100° C. in vacuo to yield an oil which was then dissolved in DCM, washed with cold water and brine, and fried with sodium sulfate. The solvent was removed in vacuo to yield an oil. The product was purified using flash chromatography (SiO2) eluting with 1% MeOH/DCM to obtain N-[4-(5-fluoro-4-indol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide as a white solid (Compound 115, 0.025 g, 16%, mp 270.0-270.5° C.).

후처리

  1. customThe solvent was removed at 100° C. in vacuo
  2. customto yield an oil which
  3. washwashed with cold water and brine
  4. customThe solvent was removed in vacuo
  5. customto yield an oil
  6. customThe product was purified
  7. washeluting with 1% MeOH/DCM

출처 및 근거

ORD 기록
ord-b3ed8c13bfda4ed6b6cc371db8ae0e00
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399462B2

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