1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67458482、化合物

HRID 1853049ノート

反応式

HRID 1853049 の反応式
[CH3:1][C:2]1[C:6]([C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[C:9]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:8]=2)=[CH:5][NH:4][N:3]=1.[CH:28]1([CH:33]=[CH:34][C:35]#[N:36])[CH2:32][CH2:31][CH2:30][CH2:29]1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH:28]1([CH:33]([N:4]2[CH:5]=[C:6]([C:7]3[N:12]4[CH:13]=[CH:14][N:15]=[C:11]4[CH:10]=[C:9]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:8]=3)[C:2]([CH3:1])=[N:3]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 178434537HCID 178434537、化合物

生成物 1

HCID 67458482HCID 67458482、化合物収率 41.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-(4-(5-(3-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine (0.0690 g, 0.191 mmol), 3-cyclopentylacrylonitrile (Table 1, compound g; 0.0696 g, 0.574 mmol) and DBU 0.0661 mL, 0.479 mmol) were suspended in DMF (3 mL) and stirred overnight. The reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc. The organics were washed with brine, dried, MgSO4 and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 0.5-2% (9:1, MeOH:NH4OH)/DCM) to furnish 3-cyclopentyl-3-(3-methyl-4-(7-(4-morpholinophenyl) imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (0.0380 g, 0.078905 mmol, 41.2% yield). MS (apci) m/z=482.2 (M+H).

後処理

  1. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc
  2. washThe organics were washed with brine
  3. customdried
  4. concentrationMgSO4 and concentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography (eluant: 0.5-2% (9:1, MeOH:NH4OH)/DCM)

出典と根拠

ORDレコード
ord-295a03ee5d0d4b4b9f19f39e634ff80f
出典データセット
uspto-grants-2015_02
特許番号
US08962596B2

反応ノート

読み込み中…