Hydrochloric Acid → HCID 67535794, compound

HRID 2382903Notes

Reaction equation

HRID 2382903 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=1.[NH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([OH:31])[CH2:26]1.Cl>CO>[CH:12]([OH:19])=[O:31].[OH:31][CH:27]1[CH2:28][CH2:29][CH2:30][CH:25]([NH:24][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=4)[N:10]=[C:6]3[CH:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=2)[CH2:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 112404593-AminocyclohexanolHCID 25212520HCID 25212520, compound

Product 1

HCID 67535794HCID 67535794, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

The title compound was prepared following procedure and work up described for example 118, but starting from N-[5-chloro-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide ((B7), 50.0 mg; 0.14 mmol; 1.00 eq) and 3-aminocyclohexanol (Betapharma, 84 mg; 0.73 mmol; 5.00 eq), heated at 120° C. HCl (1.5 M) in MeOH (2 mL) was added to the solid residue and the salt was precipitated by addition of Et2O, filtered and dried under vacuum, purified by Mass Directed AutoPrep and lyophilized to give the title compound as a mixture of cis:trans isomers as a white solid (11 mg, 18%). HPLC, Rt: 1.72 min. (purity 48.9%, isomer A), 1.87 min. (purity 46.6%, isomer B). LC/MS, M+(ESI): 420.9, M−(ESI): 418.9.

Workup

  1. customThe title compound was prepared
  2. customthe salt was precipitated by addition of Et2O
  3. filtrationfiltered
  4. customdried under vacuum
  5. custompurified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-0874c5d6863941f8a1043ee3520b2407
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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