Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)- → tert-Butyl [1-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)cyclobutyl]carbamate

HRID 876239Notes

Reaction equation

HRID 876239 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:40][C:41]1[CH:42]=[C:43]([CH:48]2[CH2:53][NH:52][CH2:51][CH:50]([NH:54][C:55](=[O:62])[C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[CH2:49]2)[CH:44]=[CH:45][C:46]=1[CH3:47]>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:40][C:41]1[CH:42]=[C:43]([CH:48]2[CH2:49][CH:50]([NH:54][C:55]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[O:62])[CH2:51][N:52]([C:13]([C:9]3([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][CH2:12]3)=[O:15])[CH2:53]2)[CH:44]=[CH:45][C:46]=1[CH3:47]

Participants

6

Reactant 3

HCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66701309N-[5-(3,4-dimethylphenyl)piperidin-3-yl]benzamide

Product 1

HCID 68075430tert-Butyl [1-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)cyclobutyl]carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

62 mg (0.3 mmol) of 1-[(tert-butoxycarbonyl)amino]cyclobutanecarboxylic acid together with 110 mg (0.3 mmol) of HATU and 47 mg (0.4 mmol) of 4-dimethylaminopyridine were initially charged in 2 ml of DMF, and 60 mg (0.2 mmol) of N-[-5-(3,4-dimethylphenyl)piperidin-3-yl]benzamide were added. The reaction mixture was stirred overnight and then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 54 mg (55% of theory)

Workup

  1. custompurified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-b546c95fcf194d1ebd45198b8ae0933b
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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