18-Crown-6 → HCID 117667385, 화합물

HRID 1526236노트

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HRID 1526236 반응식
Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].[CH2:33]([N:40]1[CH2:44][CH2:43][CH2:42][C@@H:41]1[CH2:45][OH:46])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.O.O1CCOCC1>[CH2:33]([N:40]1[CH2:44][CH2:43][CH2:42][C@@H:41]1[CH2:45][O:46][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

8

반응물 4

HCID 2855718-Crown-6HCID 719766(R)-1-N-Benzyl-prolinolHCID 23665647Potassium tert-butoxideHCID 885697085-Chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide

생성물 1

HCID 117667385HCID 117667385, 화합물수율 50.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 5-chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (300 mg), [(2R)-1-benzylpyrrolidin-2-yl]methanol (251 mg), 18-crown-6 (346 mg), potassium t-butoxide (147 mg), and dioxane (3 mL) was stirred at 100° C. for 5 hours. To the mixture were added water and ethyl acetate, followed by liquid separation. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate:chloroform=1:1) to obtain 5-{[(2R)-1-benzylpyrrolidin-2-yl]methoxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (201 mg) as a yellow solid.

후처리

  1. customfollowed by liquid separation
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate:chloroform=1:1)

출처 및 근거

ORD 기록
ord-7737effb7d70488181e35ce49d2d0d5d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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