1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-cyclopentyl-3-(4-(7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1853040ノート

反応式

HRID 1853040 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]4[CH:21]=[N:22][NH:23][CH:24]=4)[N:17]4[CH:25]=[CH:26][N:27]=[C:16]4[CH:15]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH:28]1([CH:33]=[CH:34][C:35]#[N:36])[CH2:32][CH2:31][CH2:30][CH2:29]1.N1CCCN2CCCCCC=12>CN(C=O)C>[CH:28]1([CH:33]([N:23]2[CH:24]=[C:20]([C:18]3[N:17]4[CH:25]=[CH:26][N:27]=[C:16]4[CH:15]=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([CH:5]5[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]5)=[CH:9][CH:10]=4)[N:19]=3)[CH:21]=[N:22]2)[CH2:34][C:35]#[N:36])[CH2:32][CH2:31][CH2:30][CH2:29]1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 534011163-Cyclopentylprop-2-enenitrile2 回HCID 674561367-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

生成物 1

HCID 674556573-cyclopentyl-3-(4-(7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile収率 55.19%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

7-(4-(1-Methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (0.130 g, 0.363 mmol) and 3-cyclopentylacrylonitrile (Table 1, compound g; 0.220 g, 1.81 mmol) were suspended in DMF (10 mL) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.2169 mL, 1.451 mmol) added in one portion. The reaction mixture was stirred at ambient temperature for 66 hours. The reaction mixture was partitioned between saturated aqueous 1 N NaOH and EtOAc. The organics were washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 2-6% (9:1, MeOH:NH4OH)/DCM) to furnish 3-cyclopentyl-3-(4-(7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (0.096 g, 0.200 mmol, 55.19% yield). MS (apci) m/z=480.3 (M+H).

後処理

  1. customThe reaction mixture was partitioned between saturated aqueous 1 N NaOH and EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography (eluant: 2-6% (9:1, MeOH:NH4OH)/DCM)

出典と根拠

ORDレコード
ord-b1c9477b76254143b17d951226c4209c
出典データセット
uspto-grants-2015_02
特許番号
US08962596B2

反応ノート

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