Water → HCID 59363383, compound

HRID 906028Notes

Reaction equation

HRID 906028 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13][C:14]([NH:16][C:17]2[N:18]=[C:19]3[CH:25]=[CH:24][N:23](COCC[Si](C)(C)C)[C:20]3=[N:21][CH:22]=2)=[O:15])[CH2:8]1)(=[O:6])=[O:5].O.C(N)CN>Cl.C(O)(=O)C>[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13][C:14]([NH:16][C:17]2[N:18]=[C:19]3[CH:25]=[CH:24][NH:23][C:20]3=[N:21][CH:22]=2)=[O:15])[CH2:8]1)(=[O:5])=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 3301EthylenediamineHCID 67386184HCID 67386184, compound

Product 1

HCID 59363383HCID 59363383, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

1-[(S)-1-(2,2-Dimethyl-propane-1-sulfonyl)-piperidin-3-yl]-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.045 g, 0.086 mmol) was dissolved in 1M HCl in acetic acid (0.9 mL) and stirred at 60° C. After 1.5 hours the solvent was evaporated and the residue was dried under high vacuum. The remaining oil was taken up in MeOH:H2O:EtN 8:1:1 (0.9 mL) and ethylenediamine (0.029 mL, 0.429 mmol) was added. The yellow solution stirred at RT overnight. The solvent was evaporated and the residue was purified by SiO2 chromatography (8 g SiO2, DCM:MeOH 0 to 5% MeOH) to give 0.025 g of 1-[(S)-1-(2,2-dimethyl-propane-1-sulfonyl)-piperidin-3-yl]-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as an off-white solid (74% yield).

Workup

  1. customAfter 1.5 hours the solvent was evaporated
  2. customthe residue was dried under high vacuum
  3. stirringThe yellow solution stirred at RT overnight
  4. customThe solvent was evaporated
  5. customthe residue was purified by SiO2 chromatography (8 g SiO2, DCM:MeOH 0 to 5% MeOH)

Sources & evidence

ORD record
ord-693e019aaf844f10883fbee85892a992
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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