Hydrogen chloride-ethyl acetate → 2-[2-(4-{[3-chloro-4-(piperidin-4-yloxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate dihydrochloride

HRID 1787074Notes

Reaction equation

HRID 1787074 reaction equation
[ClH:1].C(OCC)(=O)C.[C:8]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][N:22]1[C:30]2[C:29]([NH:31][C:32]3[CH:51]=[CH:50][C:35]([O:36][CH:37]4[CH2:42][CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]4)=[C:34]([Cl:52])[CH:33]=3)=[N:28][CH:27]=[N:26][C:25]=2[CH:24]=[CH:23]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[ClH:52].[ClH:1].[C:8]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][N:22]1[C:30]2[C:29]([NH:31][C:32]3[CH:51]=[CH:50][C:35]([O:36][CH:37]4[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]4)=[C:34]([Cl:52])[CH:33]=3)=[N:28][CH:27]=[N:26][C:25]=2[CH:24]=[CH:23]1)(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67520588tert-butyl 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}piperidine-1-carboxylate

Product 1

HCID 675206272-[2-(4-{[3-chloro-4-(piperidin-4-yloxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4N Hydrochloric acid/ethyl acetate solution (20 mL) and ethanol (10 mL) were added to tert-butyl 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}piperidine-1-carboxylate (3.82 g), and the mixture was stirred at room temperature for 5 hrs. The reaction mixture was concentrated under reduced pressure, and the obtained residue was crystallized from ethanol-ethyl acetate to give the title compound (3.68 g) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was crystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-61723fdf027b4fffbd014f52b48ec0c5
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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