4-Chloropyridine-2-carboxylic acid → HCID 23577249, compound

HRID 1351508Notes

Reaction equation

HRID 1351508 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.[NH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:15][CH2:14]1>CS(C)=O.C(=O)(O)[O-].[Na+]>[CH2:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([CH2:12][NH:11][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=2)[CH2:14][CH2:15]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 2308904-Chloropyridine-2-carboxylic acidHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 23577249HCID 23577249, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-chloropicolinic acid (0.8 gm, 0.0051 mol) in DMSO (4 mL) was added benzyl 4-(aminomethyl)piperidine-1-carboxylate (2.5 gm, 0.010 mol) and the mixture warmed to 140° C. for 18 h. The reaction was cooled and diluted with 10% sodium bicarbonate (100 mL) and washed with ether (2×25 mL). The aqueous extract was washed with dichloromethane (3×50 mL), and the dichloromethane extract dried over sodium sulfate and concentrated to an oil (2.4 gm). The oil was chromatographed on silica using dichloromethane/methanol/acetic acid/water-90/10/1/1 to give 4-[(1-benzyloxycarbonyl-piperidin-4-ylmethyl)-amino]-pyridine-2-carboxylic acid.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with ether (2×25 mL)
  3. extractionThe aqueous extract
  4. washwas washed with dichloromethane (3×50 mL)
  5. extractionthe dichloromethane extract
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to an oil (2.4 gm)
  8. customThe oil was chromatographed on silica

Sources & evidence

ORD record
ord-3b735ba6360f4c0dad68afa2242003f8
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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