N-Methylpiperidine → HCID 68452501, compound

HRID 2244479Notes

Reaction equation

HRID 2244479 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][O:12][C:13]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:14]=1[CH2:15][C:16]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:17]=1[O:18][CH2:19][C:20](O)=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33]CN(C(C)C)C(C)C.CN(C(ON1N=[N:57][C:52]2C=[CH:54][CH:55]=[N:56][C:51]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCCCC1>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[CH2:11][O:12][C:13]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:14]=1[CH2:15][C:16]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:17]=1[O:18][CH2:19][C:20]([N:56]1[CH2:51][CH2:52][N:57]([CH3:33])[CH2:54][CH2:55]1)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 12291N-MethylpiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68453158HCID 68453158, compound2×

Product 1

HCID 68452501HCID 68452501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(2-benzyloxycarbonylmethoxy-5-chloro-benzyl)-4-chloro-phenoxy]-acetic acid (Intermediate C) (0.1 g, 0.211 mmol) in DCM (1 mL) is added DIPEA (37 μL, 0.211 mmol) and HATU (80 mg, 0.211 mmol). After stirring at RT for 1 hour, the reaction mixture is treated with 1-methyl piperidine (24 μL, 0.211 mmol) and allowed to stir at RT for 2 days. The resulting solution is purified by chromatography on silica eluting with EtOAc/MeOH (95:5) to yield the titled product.

Workup

  1. stirringto stir at RT for 2 days
  2. customThe resulting solution is purified by chromatography on silica eluting with EtOAc/MeOH (95:5)

Sources & evidence

ORD record
ord-5949d14e5af6473882d12b4413ba17a2
Source dataset
uspto-grants-2010_03
Patent number
US07678826B2

Reaction notes

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