Hydrochloric Acid → HCID 71495246, compound

HRID 588052Notes

Reaction equation

HRID 588052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=2[NH:16][CH:17]2[CH2:22][CH2:21][N:20](C(=O)NOC(C)(C)C)[CH2:19][CH2:18]2)[CH:5]=[CH:6][CH:7]=1.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=2[NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90386490HCID 90386490, compound

Product 1

HCID 71495246HCID 71495246, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.0 g of N-(3-chlorophenyl)-2-(1-tert-butoxycarbamoylpiperidin-4-ylamino)nicotinamide obtained in Example 6, in 10 ml of ethanol was mixed with 5 ml of a conc. HCl aqueous solution and stirred for 8 hrs under reflux. The reaction solution was cooled to a room temperature, concentrated in a reduced pressure to remove the solvent, and adjusted to a pH of 9˜10 by dropwise adding saturated sodium hydrogen carbonate aqueous solution. After three rounds of extraction with 30 ml of ethylacetate per round, the extracts were dried over a desiccant to remove water, and concentrated in a reduced pressure and dried in vacuum to afford 0.69 g of the title compound (Yield: 89.9%). 1H NMR (CDCl3) δ 8.23 (d, 1H), 7.99 (d, 2H), 7.7 (d, 1H), 7.66 (s, 1H), 7.36 (d, 1H), 7.27 (t, 1H), 7.10 (d, 1H), 6.53-5.45 (m, 1H), 4.18-4.05 (m, 1H), 3.43 (t, 1H), 3.09 (d, 2H), 2.74 (t, 2H), 2.15-2.01 (m, 2H), 1.57-1.36 (m, 2H) ppm.

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated in a reduced pressure
  3. customto remove the solvent
  4. extractionAfter three rounds of extraction with 30 ml of ethylacetate per round, the extracts
  5. customwere dried over a desiccant
  6. customto remove water
  7. concentrationconcentrated in a reduced pressure
  8. customdried in vacuum

Sources & evidence

ORD record
ord-88c2c4290c01417ab6b149fb054c64e5
Source dataset
uspto-grants-2016_01
Patent number
US09227955B2

Reaction notes

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