4-(Boc-amino)tetrahydropyran-4-carboxylic acid → tert-Butyl [4-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)tetrahydro-2H-pyran-4-yl]carbamate

HRID 876238Notes

Reaction equation

HRID 876238 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:15]([OH:17])=O)[CH2:14][CH2:13][O: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.[CH3:42][C:43]1[CH:44]=[C:45]([CH:50]2[CH2:55][NH:54][CH2:53][CH:52]([NH:56][C:57](=[O:64])[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:51]2)[CH:46]=[CH:47][C:48]=1[CH3:49]>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:42][C:43]1[CH:44]=[C:45]([CH:50]2[CH2:51][CH:52]([NH:56][C:57]([C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)=[O:64])[CH2:53][N:54]([C:15]([C:9]3([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[O:17])[CH2:55]2)[CH:46]=[CH:47][C:48]=1[CH3:49]

Participants

6

Reactant 3

HCID 12682194-(Boc-amino)tetrahydropyran-4-carboxylic acidHCID 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 68075429tert-Butyl [4-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)tetrahydro-2H-pyran-4-yl]carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

75 mg (0.3 mmol) of 4-[(tert-butoxycarbonyl)amino]tetrahydro-2H-pyran-4-carboxylic 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 at RT and then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 46 mg (44% of theory)

Workup

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

Sources & evidence

ORD record
ord-e48a577f74bd4fbabe3df432fb9cd85c
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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