4-(1-Pyrrolidinyl)piperidine → Balamapimod

HRID 269763노트

반응식

HRID 269763 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22](F)=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[N:31]1([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34][CH2:33][CH2:32]1>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([N:39]4[CH2:40][CH2:41][CH:36]([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[CH2:37][CH2:38]4)=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1

참가 물질

4

반응물 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 234980744-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile

생성물 1

HCID 11478684Balamapimod수율 71.7%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
105 °C

실험 절차

A mixture of 150 mg (0.34 mmol) of 4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)-phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile and 316 mg (2.05 mmol) of 4-pyrrolidin-1-yl-piperidine in 1 mL of 1-methyl-2-pyrrolidinone is heated at 105° C. for 16 hours. The solvents are removed in vacuo. A 10 mL portion of water is added to the residue, from which a tan solid is precipitated out. The solid is filtered off and washed with water. After drying in vacuo, the solid is suspended in ethyl acetate and stirred for 1 hour. The solid is filtered off, washed with ethyl acetate and dried in vacuo to provide 140 mg of 4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)-phenylamino]-6-methoxy-7-(4-pyrrolidin-1-yl-piperidin-1-yl)-quinoline-3-carbonitrile as a yellow solid, mp 225-229° C.

후처리

  1. customThe solvents are removed in vacuo
  2. additionA 10 mL portion of water is added to the residue, from which a tan solid
  3. customis precipitated out
  4. filtrationThe solid is filtered off
  5. washwashed with water
  6. customAfter drying in vacuo
  7. filtrationThe solid is filtered off
  8. washwashed with ethyl acetate
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-5e993a61203246509d41e42f5748b5aa
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449460B2

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