Hydrochloric Acid → [(3RS, 4RS)-3-(4-Chloro-phenyl)-4-(5-chloro-pyridin-2-yloxymethyl)-piperidin-1-yl]-[4-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanone

HRID 2191103Notes

Reaction equation

HRID 2191103 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[O:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:49][C:50]1[CH:51]=[CH:52][C:53]([O:56][CH2:57][CH:58]2[CH2:63][CH2:62][NH:61][CH2:60][CH:59]2[C:64]2[CH:69]=[CH:68][C:67]([Cl:70])=[CH:66][CH:65]=2)=[N:54][CH:55]=1.Cl>CN(C=O)C>[Cl:70][C:67]1[CH:68]=[CH:69][C:64]([CH:59]2[CH:58]([CH2:57][O:56][C:53]3[CH:52]=[CH:51][C:50]([Cl:49])=[CH:55][N:54]=3)[CH2:63][CH2:62][N:61]([C:11]([C:10]3[CH:9]=[CH:8][C:7]([C:5]4[O:4][N:3]=[C:2]([CH3:1])[N:6]=4)=[CH:15][CH:14]=3)=[O:13])[CH2:60]2)=[CH:65][CH:66]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 221101114-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acidHCID 712055575-chloro-2-[(3RS, 4RS)-3-(4-chloro-phenyl)-piperidin-4-ylmethoxy]-pyridine

Product 1

HCID 68473932[(3RS, 4RS)-3-(4-Chloro-phenyl)-4-(5-chloro-pyridin-2-yloxymethyl)-piperidin-1-yl]-[4-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 18 mg (0.08 mmol) 4-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid, 43 mg (0.11 mmol) HATU, 0.1 mL DIPEA and 32 mg (0.09 mmol) 5-chloro-2-[(3RS, 4RS)-3-(4-chloro-phenyl)-piperidin-4-ylmethoxy]-pyridine; hydrochloride in 2 mL DMF was reacted at room temperature over night. The mixture was subjected to preparative HPLC purification on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 32 mg (64%) of the title compound as white foam. MS (m/e): 523.3 [(M+H)+].

Workup

  1. customThe mixture was subjected to preparative HPLC purification on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and NEt3
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions 32 mg (64%) of the title compound as white foam

Sources & evidence

ORD record
ord-f5ac34b11f384b15b857418f94b7a342
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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