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Trifluoroacetic acid → Molidustat

HRID 876696
Notes
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Reaction equation

HRID 876696 reaction equation
C(O[C:4](=[O:15])[C:5]([N:10]1[CH:14]=[CH:13][N:12]=[N:11]1)=[CH:6][N:7](C)C)C.[NH:16]([C:18]1[N:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:19]=1)N.C(O)(C(F)(F)F)=O>C(OCC)(=O)C>[N:24]1([C:20]2[N:21]=[CH:22][N:23]=[C:18]([N:16]3[C:4](=[O:15])[C:5]([N:10]4[CH:14]=[CH:13][N:12]=[N:11]4)=[CH:6][NH:7]3)[CH:19]=2)[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 13393622(6-Morpholin-4-ylpyrimidin-4-yl)hydrazineHCID 66726233Ethyl 3-(dimethylamino)-2-(1H-1,2,3-triazol-1-yl)acrylate

Product 1

HCID 59603622MolidustatYield 61.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

1.9 g (8.8 mmol) of the compound from Example 3A and 1.9 g (9.7 mmol) of the compound from Example 16A are initially introduced into 25 ml ethyl acetate and 504 mg (4.4 mmol) TFA are added at RT. The mixture is stirred under reflux for 16 h, then cooled to 5° C. and subsequently stirred for a further 2 h. The solid formed is filtered off, washed with ethyl acetate and dried first in air and thereafter under a high vacuum. 1.7 g of product are obtained.

Workup

  1. additionare added at RT
  2. temperatureunder reflux for 16 h
  3. stirringsubsequently stirred for a further 2 h
  4. customThe solid formed
  5. filtrationis filtered off
  6. washwashed with ethyl acetate
  7. customdried first in air

Sources & evidence

ORD record
ord-0dd197c44bda4080938e92af406ba908
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987261B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes