3-Aminocyclohexanol → HCID 68478959, compound

HRID 2382904Notes

Reaction equation

HRID 2382904 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]([Cl:20])[CH:3]=1.[NH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH:24]([OH:28])[CH2:23]1>>[CH:12]([OH:19])=[O:28].[Cl:20][C:4]1[CH:3]=[C:2]([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH:24]([OH:28])[CH2:23]2)[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]=1

Participants

3

Reactant 2

HCID 112404593-AminocyclohexanolHCID 25212768N-(5,7-dichloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 68478959HCID 68478959, compound

Conditions

Temperature
120 °C

Procedure

The title compound was prepared following procedure and work up described for example 118, but starting from N-(5,7-dichloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B10), 100 mg; 0.32 mmol; 1.0 eq) and 3-aminocyclohexanol (Betapharma, 187 mg; 1.62 mmol; 5.0 eq), heated at 120° C., 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 beige powder (9 mg, 7%). HPLC, Rt: 2.15 min. (purity 57.4%, isomer A), 2.28 min. (purity 34.7%, isomer B). LC/MS, M+(ESI): 386.9, M−(ESI): 384.9.

Workup

  1. customThe title compound was prepared
  2. filtrationfiltered
  3. customdried under vacuum
  4. custompurified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-2a75c91cbc2247628ed7fd092e719cf3
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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