Piperidine → HCID 178520334, compound

HRID 916054Notes

Reaction equation

HRID 916054 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([NH:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([N:19]2[CH:23]=[C:22]([C:24](O)=[O:25])[N:21]=[N:20]2)[CH2:15][CH2:14]1)=[O:11].[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([NH:12][C@H:13]1[CH2:14][CH2:15][C@@H:16]([N:19]2[CH:23]=[C:22]([C:24]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:25])[N:21]=[N:20]2)[CH2:17][CH2:18]1)=[O:11]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178520335HCID 178520335, compound

Product 1

HCID 178520334HCID 178520334, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution under Ar of 1-{cis-4-[2-(2-chloro-6-fluoro-phenyl)-acetylamino]-cyclohexyl}-1H-[1,2,3]triazole-4-carboxylic acid (100 mg) in DMF (4 ml) were added piperidine (22 mg), TBTU (93 mg) and DIPEA (0.13 ml). The solution was stirred 1 h at RT before partitioning it between EtOAc (50 ml) and H2O (50 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated. Chromatography (silica, CH2Cl2 to CH2Cl2 5% MeOH) afforded the product (112 mg, 95%). Off-white solid. MS 448.1 (100, [M+H]+).

Workup

  1. custombefore partitioning it between EtOAc (50 ml) and H2O (50 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4f609972427043258564e2abe82099f7
Source dataset
uspto-grants-2007_09
Patent number
US07268154B2

Reaction notes

Loading…