Hydrogen chloride-ethyl acetate → HCID 71113939, compound

HRID 57652Notes

Reaction equation

HRID 57652 reaction equation
[F:1][C:2]1([F:38])[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH:3]1[CH2:15][NH:16][C:17]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[CH:20]=[C:19]([C:27]2[CH:32]=[CH:31][C:30]([N:33]([CH2:35][CH2:36][OH:37])[CH3:34])=[CH:29][CH:28]=2)[N:18]=1.Cl.CC(=O)OCC>CC(=O)OCC>[F:38][C:2]1([F:1])[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[CH2:15][NH:16][C:17]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[CH:20]=[C:19]([C:27]2[CH:32]=[CH:31][C:30]([N:33]([CH3:34])[CH2:35][CH2:36][OH:37])=[CH:29][CH:28]=2)[N:18]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71113935Tert-butyl 4,4-difluoro-3-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 71113939HCID 71113939, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4,4-difluoro-3-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl) pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate (25 mg, 0.05 mmol) and 2 mL of HCl-EA (5.0 N) in 4 mL of EA was stirred at room temperature for 1.5 hours. The volatiles were removed in vacuo, and the residue was added to 5 mL of MeOH and 0.5 mL of NH3.H2O. The volatiles were removed in vacuo, and the residue was purified by chromatography with MeOH/H2O (1:10-5:1) to give 14 mg of title compound. MS (m/z)=429 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was added to 5 mL of MeOH and 0.5 mL of NH3.H2O
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified by chromatography with MeOH/H2O (1:10-5:1)

Sources & evidence

ORD record
ord-3dd19660fe474369a0d1b33a6638f0ee
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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