Ethylenediamine → HCID 46234567, compound

HRID 906004Notes

Reaction equation

HRID 906004 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([Cl: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]([Cl: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 67385304HCID 67385304, compound

Product 1

HCID 46234567HCID 46234567, compoundYield 16.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 23434731Methanol water triethylamineSolvent

Conditions

Temperature
50 °C

Procedure

1-Cyclohexyl-3-[7-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (44 mg, 0.104 mmol) was dissolved in a solution of HCl in AcOH (1M, 2.1 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 (69 ul, 1.04 mmol) was added. The reaction mixture was stirred for 5 days, concentrated and purified by SiO2 chromatography (8 g SiO2, DCM/MeOH 0 to 10% MeOH) to give 5 mg of 1-cyclohexyl-3-(7-chloro-5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as a white solid (16% 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 to 10% MeOH)

Sources & evidence

ORD record
ord-3c0680b3f4374e11b80aa5b541e39fa0
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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