1-Aminopiperidine → HCID 44390716, compound

HRID 916943Notes

Reaction equation

HRID 916943 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([OH:17])=O)=[CH:13][C:12]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>[N:34]1([NH:33][C:15]([C:14]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:10][C:11]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[Cl:32])=[C:12]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[CH:13]=2)=[O:17])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 69415176HCID 69415176, compound

Product 1

HCID 44390716HCID 44390716, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 2-(benzyloxy)-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylic acid (30 mg, 0.062 mmol) from Step A in methylene chloride (1 mL) was added 1-aminopiperidine (9.3 mg, 0.093 mmol), DIPEA (0.016 mL, 0.093 mmol) and PyBOP (17.4 mg, 0.093 mmol). The reaction was stirred at rt for 20 h and was then diluted with aq. saturated sodium carbonate and extracted twice with methylene chloride. The organic layers were washed with a portion of brine and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC eluted with 50% ethyl acetate in hexanes to yield N-(piperidin-1-yl)-2-(benzyloxy)-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxamide as the slower eluting band. HPLC/MS: 566 (M+1), 568 (M+3); Rt=4.56 min; 1HNMR (CDCl3): δ 1.2-1.9 (4 m, 6H), 2.7-3.1 (2 m, 4H), 7.07 (m, 2H), 7.20-7.38 (m, 10H), 7.668 and 8.074 (2 s, 1H).

Workup

  1. extractionextracted twice with methylene chloride
  2. washThe organic layers were washed with a portion of brine
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC
  6. washeluted with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6eb5fbc2b64c47c5a2bd8032580f0389
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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