Hydrogen chloride-ethyl acetate → (S)-7-(4-(4-(cyclopropylsulfonyl)piperazin-1-yl)phenyl)-N-(morpholin-2-yl methyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57632Notes

Reaction equation

HRID 57632 reaction equation
[CH:1]1([S:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[N:28]=[C:27]([NH:29][CH2:30][C@@H:31]5[O:36][CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]5)[C:26]5[C:21](=[N:22][CH:23]=[CH:24][N:25]=5)[CH:20]=4)=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.Cl.CC(=O)OCC>CC(=O)OCC>[CH:1]1([S:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]4[N:28]=[C:27]([NH:29][CH2:30][C@H:31]5[O:36][CH2:35][CH2:34][NH:33][CH2:32]5)[C:26]5[C:21](=[N:22][CH:23]=[CH:24][N:25]=5)[CH:20]=4)=[CH:17][CH:18]=3)[CH2:9][CH2:8]2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86717393(S)-tert-butyl 2-((7-(4-(4-(cyclopropylsulfonyl)piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Product 1

HCID 71113927(S)-7-(4-(4-(cyclopropylsulfonyl)piperazin-1-yl)phenyl)-N-(morpholin-2-yl methyl)pyrido[4,3-b]pyrazin-5-amineYield 39.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-tert-butyl 2-((7-(4-(4-(cyclopropylsulfonyl)piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (52 mg, 0.09 mmol) and 2 mL of HCl-EA (5.0 N) in 5 mL of EA, was stirred at room temperature for 1 hour. The volatiles were removed in vacuo, and the residue was added to 5 mL of MeOH and 0.5 mL of NH3.H2O, was stirred at room temperature for 10 minutes. The volatiles were removed in vacuo, and the residue was purified by chromatography with MeOH/H2O (1:6˜5:1) to give 18 mg title compound. MS (m/z)=510 (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 (1:6˜5:1)

Sources & evidence

ORD record
ord-e33c21c651e048f698ad4a9ecb75479f
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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