L-Tartaric acid → HCID 44594314, compound

HRID 1694581Notes

Reaction equation

HRID 1694581 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C@@H:12]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=4)[O:21][CH2:22][CH2:23][OH:24])[CH2:13]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[C:28]([OH:37])(=[O:36])[C@@H:29]([C@H:31]([C:33]([OH:35])=[O:34])[OH:32])[OH:30]>C(O)C>[C:28]([OH:37])(=[O:36])[C@@H:29]([C@H:31]([C:33]([OH:35])=[O:34])[OH:32])[OH:30].[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C@@H:12]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=4)[O:21][CH2:22][CH2:23][OH:24])[CH2:13]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 44537934HCID 44537934, compound

Product 1

HCID 44594314HCID 44594314, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Crude (R)-2-(3-((3-(isoquinolin-5-ylamino)pyrrolidin-1-yl)methyl)phenoxy)ethanol (1.0 g, 2.7 mmol, from example 11) was dissolved in 11 mL of ethanol. The solution was stirred while 27.5 mL of a 0.1 M solution of L-tartaric acid in ethanol was added. After 2 hours, the resulting suspension was filtered, washed with ethanol, and dried under nitrogen. Approximately 1.1 g of (R)-2-(3-((3-(isoquinolin-5-ylamino)pyrrolidin-1-yl)methyl)phenoxy)ethanol L-tartaric acid salt was isolated as a yellow solid (79% yield).

Workup

  1. additionwas added
  2. filtrationthe resulting suspension was filtered
  3. washwashed with ethanol
  4. customdried under nitrogen

Sources & evidence

ORD record
ord-e0f18a2133b54f3ea56b933032012e75
Source dataset
uspto-grants-2012_04
Patent number
US08158796B2

Reaction notes

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