p-Toluenesulfonic acid → HCID 68508898, compound

HRID 1715125Notes

Reaction equation

HRID 1715125 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH2:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:22](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[N:21]=[CH:22]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 58380653HCID 58380653, compound

Product 1

HCID 68508898HCID 68508898, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(3-amino-pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (10.0 g, 34.20 mmol, 1.0 equiv) and triethyl orthoformate (10.14 g, 68.40 mmol, 2.0 equiv) in anhydrous toluene (70 mL) was added toluene-4-sulfonic acid (0.59 g, 3.42 mmol, 0.1 equiv) and the reaction mixture heated to reflux for 16 h. The solvent was removed by evaporation under reduced pressure and the residue triturated with diethyl ether. The preciptate was filtered off, washed with diethyl ether and dried under reduced pressure to yield 7.6 g (73%) of the title compound. 1H NMR (400 MHz, DMSO): δ 1.43 (s, 9H), 1.92-2.04 (m, 4H), 2.95 (br s, 2H), 4.13 (br s, 2H), 4.64 (t, J=3.8 Hz, 1H), 7.75 (d, J=5.5 Hz, 1H), 8.34 (d, J=5.5 Hz, 1H), 8.55 (s, 1H), 8.95 (s, 1H). MS (ISP): 303.2 [M+H]1.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 16 h
  3. customThe solvent was removed by evaporation under reduced pressure
  4. customthe residue triturated with diethyl ether
  5. filtrationThe preciptate was filtered off
  6. washwashed with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-09f30c8b8d674978bd8d4b91e445e956
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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