1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67458482, compound

HRID 1853049Notes

Reaction equation

HRID 1853049 reaction equation
[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

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 534011163-Cyclopentylprop-2-enenitrile2×HCID 178434537HCID 178434537, compound

Product 1

HCID 67458482HCID 67458482, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-295a03ee5d0d4b4b9f19f39e634ff80f
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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