Hydrochloric Acid → HCID 52932175, compound

HRID 1626804Notes

Reaction equation

HRID 1626804 reaction equation
C([O:5][C:6](=[O:43])[CH2:7][NH:8][C:9]([C:11]1[C:16]([OH:17])=[C:15]([CH3:18])[N:14]=[C:13]([CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[CH:42]=[CH:41][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][N:33]=4)=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)[N:12]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O.Cl>ClCCl>[CH2:39]([O:38][C:36]([C:35]1[CH:41]=[CH:42][C:32]([C:29]2[CH:30]=[CH:31][C:26]([N:23]3[CH2:24][CH2:25][CH:20]([CH2:19][C:13]4[N:12]=[C:11]([C:9]([NH:8][CH2:7][C:6]([OH:43])=[O:5])=[O:10])[C:16]([OH:17])=[C:15]([CH3:18])[N:14]=4)[CH2:21][CH2:22]3)=[CH:27][CH:28]=2)=[N:33][CH:34]=1)=[O:37])[CH3:40]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 68193184HCID 68193184, compound

Product 1

HCID 52932175HCID 52932175, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 6-{4-[4-({4-[(2-tert-butoxy-2-oxoethyl)carbamoyl]-5-hydroxy-6-methylpyrimidin-2-yl}methyl)piperidin-1-yl]phenyl}nicotinate (0.043 g, 0.073 mmol) was dissolved in dichloromethane (5 mL), and trifluoroacetic acid (5 mL) was added at room temperature, followed by stirring for 12 hours. Hydrochloric acid (1 M) was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the organic layer was concentrated under reduced pressure. After the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: ethyl acetate/methanol), a fraction corresponding to the Rf value=0.10 (ethyl acetate/methanol=4/1) by thin layer chromatography was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, followed by addition of diisopropyl ether, and subsequently the deposited solid was collected by filtration using diisopropyl ether to afford the title compound (0.020 g, 0.037 mmol) as a pale yellow solid (yield 51%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationsubsequently the organic layer was concentrated under reduced pressure
  3. customAfter the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: ethyl acetate/methanol)
  4. concentrationa fraction corresponding to the Rf value=0.10 (ethyl acetate/methanol=4/1) by thin layer chromatography was concentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in ethyl acetate
  6. additionfollowed by addition of diisopropyl ether
  7. filtrationsubsequently the deposited solid was collected by filtration

Sources & evidence

ORD record
ord-a0ece821b8d2426cb39d0d91f51a6ff8
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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