(2R)-2-methoxypropanoic acid → HCID 66761992, compound

HRID 876317Notes

Reaction equation

HRID 876317 reaction equation
[CH3:1][O:2][C@H:3]([CH3:7])[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:32][C:33]([F:57])([F:56])[O:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:46][NH:45][CH2:44][CH:43]([NH:47][C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:42]2)=[CH:37][CH:36]=1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:1][O:2][C@H:3]([CH3:7])[C:4]([N:45]1[CH2:46][CH:41]([C:38]2[CH:39]=[CH:40][C:35]([O:34][C:33]([F:57])([F:32])[F:56])=[CH:36][CH:37]=2)[CH2:42][CH:43]([NH:47][C:48]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[O:55])[CH2:44]1)=[O:6]

Participants

6

Reactant 3

HCID 2733584(2R)-2-methoxypropanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66701272N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide

Product 1

HCID 66761992HCID 66761992, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

44 mg (0.41 mmol) of (2R)-2-methoxypropanoic acid together with 157 mg (0.41 mmol) of HATU and 67 mg (0.55 mmol) of 4-dimethylaminopyridine were initially charged in 2 ml of DMF, and 100 mg (0.27 mmol) of N-{5-[4-(trifluoromethoxy)phenyl]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: 116 mg (94% of theory)

Workup

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

Sources & evidence

ORD record
ord-de040018c16d4c319c51f33121d94fb8
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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