Hydrochloric Acid → HCID 68538023, compound

HRID 1993699Notes

Reaction equation

HRID 1993699 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([NH:21][C:22]([NH:24][C:25]3[N:26]([C:34]4[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=4)[N:27]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:29]=3)=[O:23])[CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CCOC(C)=O.Cl>C(Cl)Cl>[C:30]([C:28]1[CH:29]=[C:25]([NH:24][C:22]([NH:21][C:19]2[CH:18]=[CH:17][N:16]=[C:15]([O:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:20]=2)=[O:23])[N:26]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)[N:27]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 68540874HCID 68540874, compound

Product 1

HCID 68538023HCID 68538023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of 4-{4-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (877 mg, 1.6 mmol) in 1:1 EtOAc:DCM (100 mL) with a bubbling stream of HCl (g) for 3 min. Allow the resulting mixture to stand for 30 min, then concentrate under reduced pressure. Dissolve the residue in MeOH and load onto a 20 g Varian SCX column, rinsing well with MeOH. Elute the free base with 1:1 DCM:2 M ammonia in MeOH. Concentrate the solution under reduced pressure to give the title compound in quantitative yield. LCMS ES+(m/z) 449 [M+H].

Workup

  1. concentrationconcentrate under reduced pressure
  2. dissolutionDissolve the residue in MeOH
  3. washload onto a 20 g Varian SCX column, rinsing well with MeOH
  4. washElute the free base with 1:1 DCM
  5. concentrationConcentrate the solution under reduced pressure

Sources & evidence

ORD record
ord-beb09a132f574514a8e77e789e43f42e
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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