Hydrochloric Acid → HCID 58016009, compound

HRID 2189328Notes

Reaction equation

HRID 2189328 reaction equation
[CH2:1]([CH:3]([N:6]1[C:10]2[N:11]=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25](C(=O)C)[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[CH:31]([OH:33])[CH3:32])[CH2:4][CH3:5])[CH3:2].Cl.[CH3:35]O>O1CCOCC1>[CH2:4]([CH:3]([N:6]1[C:10]2[N:11]=[C:12]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[CH:20][CH:21]=3)[N:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[CH:31]([O:33][CH3:35])[CH3:32])[CH2:1][CH3:2])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58015909HCID 58015909, compound

Product 1

HCID 58016009HCID 58016009, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(4-{4-[7-(1-ethyl-propyl)-6-(1-hydroxy-ethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone (19 mg, 0.042 mmol) in MeOH (1 mL) is added 4N HCl in dioxane (1 mL). The reaction mixture is stirred at 60° C. for 2 h. The mixture is loaded on Solid Phase Extraction column (Sorbent: benzenesulfonic acid), washed with MeOH, eluted with EtOAc:MeOH:Et3N (1:1:0.05), concentrated in vacuo. The residue is purified by preparative HPLC to give 10 mg of [7-(1-ethyl-propyl)-6-(1-methoxy-ethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl]-(4-piperazin-1-yl-phenyl)-amine.

Workup

  1. extractionThe mixture is loaded on Solid Phase Extraction column (Sorbent: benzenesulfonic acid)
  2. washwashed with MeOH
  3. washeluted with EtOAc:MeOH:Et3N (1:1:0.05)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-dff518103771464590d4b7f28f293523
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

Loading…