Ethanol → (S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid esylate

HRID 1620398Notes

Reaction equation

HRID 1620398 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][C@H:20]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[N:32]3[CH:36]=[CH:35][C:34]([CH3:37])=[N:33]3)[C:21]([F:24])([F:23])[F:22])[N:16]=[C:15]([NH2:38])[N:14]=2)=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[CH2:39]([S:41]([OH:44])(=[O:43])=[O:42])[CH3:40].CC(O)C.CCO>CO>[S:41]([CH2:39][CH3:40])([OH:44])(=[O:43])=[O:42].[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][C@H:20]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[N:32]3[CH:36]=[CH:35][C:34]([CH3:37])=[N:33]3)[C:21]([F:23])([F:24])[F:22])[N:16]=[C:15]([NH2:38])[N:14]=2)=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 3776IsopropanolHCID 11668Ethanesulfonic acidHCID 25025298Telotristat

Product 1

HCID 57331288(S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid esylateYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with 0.5 mL of (S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid free base (0.05 M, 0.025 mmol) in MeOH, and 0.28 mL ethanesulfonic acid in IPA (0.1N, 0.028 mmol, 1.1 equiv.). After the solvent was evaporated, 0.75 mL MeCN was added and stirred to give a suspension, followed by adding 0.2 mL EtOH and heated until the solid was completely dissolved. After stirring overnight, the crystal was filtered off, washed with heptane (0.6 mL), dried at 45° C. under vacuum to give (S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid esylate (69% yield).

Workup

  1. customAfter the solvent was evaporated
  2. addition0.75 mL MeCN was added
  3. customto give a suspension
  4. temperatureheated until the solid
  5. dissolutionwas completely dissolved
  6. stirringAfter stirring overnight
  7. filtrationthe crystal was filtered off
  8. washwashed with heptane (0.6 mL)
  9. customdried at 45° C. under vacuum

Sources & evidence

ORD record
ord-1c6b1f9d7b71498f973024a9f340f563
Source dataset
uspto-grants-2014_07
Patent number
US08772483B2

Reaction notes

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