Hydrochloric Acid → HCID 58619020, compound

HRID 1795302Notes

Reaction equation

HRID 1795302 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][C@H:14]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]1=[O:26])C.[Li+].[OH-].Cl>>[Cl:12][C:11]1[N:6]([CH2:5][C:4]([OH:27])=[O:3])[C:7](=[O:26])[C:8]([NH:13][C@H:14]([CH2:22][N:23]([CH3:24])[CH3:25])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:9][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69589985HCID 69589985, compound

Product 1

HCID 58619020HCID 58619020, compound

Procedure

To a solution of [6-chloro-(S)-3-(1-dimethylaminomethyl-2-phenyl-ethylamino)-2oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester (385 mg, 0.98 mmol) in THP (6 ml) is added 1N LiOH (1.27 ml, 1.27 mmol) and the reaction mixture is stirred at room temperature for 3 h. To the reaction mixture is added 1N HCl (1.27 ml, 1.27 mmol) and the reaction mixture is concentrated in vacuo, azeotroped with methanol and dried on high vacuum to give [6-chloro-(S)-3-(1-dimethylaminomethyl-2-phenylethylamino)-2-oxo-2H-pyrazin-1-yl)-acetic acid as a white solid which contains 1.3 eq LiCl. 1H NMR (CD3OD, 400 MHz): δ 7.30–7.15 (m, 5H); 6.86 (s, 1H); 4.80 (A of AB, d, J=16.7 Hz, 1H); 4.76–4.66 (m, 1H); 4.56 (B of AB, d, J=16.7 Hz, 1H); 3.45 (A of ABX, dd, J=13, 12.9 Hz, 1H); 3.25 (B of ABX, dd, J=13, 3.4 Hz, 1H); 3.00–2.85 (m, 2H).

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customazeotroped with methanol
  3. customdried on high vacuum

Sources & evidence

ORD record
ord-70cbc5356890432bb49163cdfa052d6f
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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