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Cyclohexylamine → [2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl][2-(cyclohexylamino)ethyl]amine

HRID 2121603
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HRID 2121603 반응식
[CH3:1][C:2]1[N:3]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][CH2:12][CH2:13]Cl)[CH:7]=[C:6]([CH3:15])[N:5]=2.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CN1C(=O)CCC1>[CH3:1][C:2]1[N:3]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][CH2:12][CH2:13][NH:31][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH:7]=[C:6]([CH3:15])[N:5]=2
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반응물 2

HCID 7965CyclohexylamineHCID 22034113[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl](2-chloroethyl)amine

생성물 1

HCID 22034117[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl][2-(cyclohexylamino)ethyl]amine

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Heat a solution of [2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-y1](2-chloroethyl)amine (0.04 g, 0.12 mmol), and cyclohexyl amine (0.13 mL g, 1.16 mmol) in dry NMP (2 mL) at 80° C. for 20 h. Pour the cooled mixture onto water (20 mL) and extract twice with ethyl acetate (20 mL). Wash the combined extracts with brine (20 mL), dry, and evaporate in vacuo. Purify by flash column chromatography (10% methanol in CH2Cl2 with 0.1% ammonium hydroxide) to obtain the title compound as a white solid.

후처리

  1. additionPour the cooled mixture onto water (20 mL)
  2. extractionextract twice with ethyl acetate (20 mL)
  3. washWash the combined extracts with brine (20 mL)
  4. customdry
  5. customevaporate in vacuo
  6. customPurify by flash column chromatography (10% methanol in CH2Cl2 with 0.1% ammonium hydroxide)

출처 및 근거

ORD 기록
ord-0e94bfc348074dd68605e87b5a59d9e7
출처 데이터셋
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06696445B2

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