Ethylenediamine → HCID 46233739, compound

HRID 905998Notes

Reaction equation

HRID 905998 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([CH3:20])=[CH:18][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[C:19]([CH3:20])=[CH:18][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 67385884HCID 67385884, compound

Product 1

HCID 46233739HCID 46233739, compoundYield 27.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 23434731Methanol water triethylamineSolvent

Conditions

Temperature
50 °C

Procedure

1-Cyclohexyl-3-[7-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (38 mg, 0.094 mmol) was dissolved in a solution of HCl in AcOH (1M, 1.9 mL), and heated at 50° C. in the sealed tube overnight. The reaction mixture was concentrated to dryness, dissolved in 1 mL of MeOH:H2O:Et3N 8:1:1 and ethylenediamine (63 ul, 0.94 mmol) was added. The reaction mixture was stirred overnight, concentrated and purified by SiO2 chromatography (8 g SiO2, DCM/MeOH 0-5% MeOH) to give 7 mg of 1-cyclohexyl-3-(7-methyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as a white solid (27% yield).

Workup

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

Sources & evidence

ORD record
ord-a1858da9c4ed42c6b15085834b27ef96
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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