Triethylamine → HCID 53308229, compound

HRID 1846670Notes

Reaction equation

HRID 1846670 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]2)=[C:4]([NH:18][C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH:3]=1.[OH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([N:32]2[CH2:33][CH2:34][CH:29]([OH:28])[CH2:30][CH2:31]2)=[O:17])[CH2:12][CH2:13]1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68304433HCID 68304433, compound

Product 1

HCID 53308229HCID 53308229, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.100 g (0.246 mmol) of {1-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-piperidin-4-yl}-acetic acid, 0.124 g (1.23 mmol) of 4-hydroxypiperdine, 0.10 g (0.32 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, and 0.10 mL (0.74 mmol) of triethylamine in N,N-dimethylformamide (3 mL) are stirred at room temperature for 3 hours. The mixture is concentrated under reduced pressure and the residue is purified by preparative reverse phase HPLC to provide 0.040 g (33%) of the title compound (278) as a colorless solid. [M+H]+=490.2.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customthe residue is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-95962ff652924746bd748a0184b7e07d
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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