Cyclohexyl isocyanate → HCID 67385884, compound

HRID 905997Notes

Reaction equation

HRID 905997 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH2:11])[N:9]=2)[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1.[CH:20]1([N:26]=[C:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>ClCCCl>[CH:20]1([NH:26][C:27]([NH:11][C:8]2[N:9]=[C:10]3[C:2]([CH3:1])=[CH:3][N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:18])([CH3:17])[CH3:19])[C:5]3=[N:6][CH:7]=2)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 67385777HCID 67385777, compound

Product 1

HCID 67385884HCID 67385884, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7-Methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (41 mg, 0.147 mmol) was dissolved in 1,2-dichloroethane (1.5 mL). Cyclohexylisocyanate (0.19 mL, 1.47 mmol) was added and the reaction mixture was heated to reflux for 64 hr, cooled to RT, concentrated, purified by SiO2 chromatography (8 g SiO2, hexanes/EtOAc 0-50% EtOAc) to give 38 mg of 1-cyclohexyl-3-[7-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as a white solid (64% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 64 hr
  3. concentrationconcentrated
  4. custompurified by SiO2 chromatography (8 g SiO2, hexanes/EtOAc 0-50% EtOAc)

Sources & evidence

ORD record
ord-bbb1ca87c85c46fdb461b38d822184f2
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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