Ethylenediamine → 1-cyclohexyl-3-(6-methyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea

HRID 905991Notes

Reaction equation

HRID 905991 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[CH:19]=[C:18]([CH3:20])[N:17](COCC[Si](C)(C)C)[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N)CN>Cl.CC(O)=O.CO.O.CCN(CC)CC>[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[CH:19]=[C:18]([CH3:20])[NH:17][C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 3301EthylenediamineHCID 673861051-cyclohexyl-3-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Product 1

HCID 462337381-cyclohexyl-3-(6-methyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-ureaYield 32%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 23434731Methanol water triethylamineSolvent

Conditions

Temperature
50 °C

Procedure

1-Cyclohexyl-3-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (56 mg, 0.139 mmol) was dissolved in a solution of HCl in AcOH (1M, 2.8 mL), and heated at 50° C. in the sealed tube overnight. The reaction mixture was concentrated to dryness, dissolved in 1.5 mL of MeOH:H2O:Et3N 8:1:1 and ethylenediamine (93 ul, 1.39 mmol) was added. The reaction mixture was stirred overnight, concentrated and purified by and purified by SiO2 chromatography (8 g SiO2, DCM/MeOH 0-5% MeOH) to give 12 mg of 1-cyclohexyl-3-(6-methyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as a white solid (32% yield).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionwas added
  3. concentrationconcentrated
  4. custompurified by and
  5. custompurified by SiO2 chromatography (8 g SiO2, DCM/MeOH 0-5% MeOH)

Sources & evidence

ORD record
ord-82f22141824f4bdc8e5566ff2896f554
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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