Sodium borohydride → HCID 58397906, compound

HRID 451584Notes

Reaction equation

HRID 451584 reaction equation
[NH2:1][C:2]1[N:21]=[C:5]2[C:6]([C:10]3([OH:20])[CH2:15][CH2:14][CH:13]([C:16]([F:19])([F:18])[F:17])[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:22][C:23]1[N:27]=[C:26]([N:28]2[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)[S:25][N:24]=1.[BH4-].[Na+]>C(O)C>[CH3:22][C:23]1[N:27]=[C:26]([N:28]2[CH2:29][CH2:30][CH:31]([NH:1][C:2]3[N:21]=[C:5]4[C:6]([C:10]5([OH:20])[CH2:11][CH2:12][CH:13]([C:16]([F:17])([F:18])[F:19])[CH2:14][CH2:15]5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)[CH2:32][CH2:33]2)[S:25][N:24]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 592585101-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-oneHCID 67343780HCID 67343780, compound

Product 1

HCID 58397906HCID 58397906, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared in analogy to example 219f), starting from 1-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-4-(trifluoromethyl)cyclohexanol and 1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-one. As a reducing agent 4 equivalent sodium borohydride in ethanol was used at 70° C. over night. The title compound was obtained after column chromatography on silica gel using ethyl acetate as eluent as a white solid (yield: 46%).

Workup

  1. customPrepared in analogy to example 219f),

Sources & evidence

ORD record
ord-cba8a9b93a984b99abdbc3f78c6b508c
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

Loading…