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4-Methylmorpholine → (Rac)-(3-diethylamino-pyrrolidin-1-yl)-[2-(3-hexyl-phenyl)-5-iodo-3-methyl-3h-imidazol-4-yl]-methanone

HRID 545366
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HRID 545366 반응식
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:17]([CH3:18])[C:16]([C:19]([OH:21])=O)=[C:15]([I:22])[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[CH2:41]([N:43]([CH2:49][CH3:50])[CH:44]1[CH2:48][CH2:47][NH:46][CH2:45]1)[CH3:42]>CC#N>[CH2:41]([N:43]([CH2:49][CH3:50])[CH:44]1[CH2:48][CH2:47][N:46]([C:19]([C:16]2[N:17]([CH3:18])[C:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=3)=[N:14][C:15]=2[I:22])=[O:21])[CH2:45]1)[CH3:42]
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참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 199619953-(Diethylamino)pyrrolidineHCID 671332392-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acid2회

생성물 1

HCID 57541119(Rac)-(3-diethylamino-pyrrolidin-1-yl)-[2-(3-hexyl-phenyl)-5-iodo-3-methyl-3h-imidazol-4-yl]-methanone수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

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온도
0 °C

실험 절차

A solution of 0.41 g (1.0 mmol) of 2-(3-hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-carboxylic acid (intermediate 1) in 10 ml of MeCN was treated with 0.192 g (1.1 mmol) of 2-chloro-4,6-dimethoxy-[1,3,5]triazine and cooled down to 0° C. 0.33 ml=0.30 g (3.0 mmol) of N-methylmorpholine was added and stirring continued at 0° C. for another 2 hours. Then, a solution of 0.159 g (1.1 mmol) of (rac)-diethyl-pyrrolidin-3-yl-amine in 5 ml of MeCN was added and the reaction mixture was allowed the reach RT. After stirring at RT for 18 hours, it was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.39 g (73%) of the title compound as light brown oil. MS: 537.3 (MH+).

후처리

  1. customthe reach RT
  2. stirringAfter stirring at RT for 18 hours
  3. additionit was poured
  4. extractionextracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

출처 및 근거

ORD 기록
ord-acf2627b64804c768efe36e784304fb2
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935707B2

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