Hydrochloric Acid → HCID 59134447, compound

HRID 1993689Notes

Reaction equation

HRID 1993689 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([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]4([CH3:33])[CH2:32][CH2:31]4)[CH:29]=3)=[O:23])=[C:17]([CH3:41])[N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C(OCC)(=O)C>ClCCl>[CH3:33][C:30]1([C:28]2[CH:29]=[C:25]([NH:24][C:22]([NH:21][C:18]3[C:17]([CH3:41])=[N:16][C:15]([N:12]4[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]4)=[CH:20][CH:19]=3)=[O:23])[N:26]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[N:27]=2)[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 68540889HCID 68540889, compound

Product 1

HCID 59134447HCID 59134447, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bubble gaseous hydrochloric acid through a solution of 4-(6-methyl-5-{3-[5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-ureido}-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (assume 2.74 mmol) in 1:1 ethyl acetate:dichloromethane (200 mL) for 3 min to ensure saturation. Allow the mixture to stand for 30 min then concentrate under reduced pressure to a white solid. Dissolve the solid in MeOH and load onto a 20 g Varian SCX column, rinsing with additional MeOH. Elute the free base with 1:1 2 M ammonia in MeOH:dichloromethane. Concentrate the solution under reduced pressure to give a white solid (1.21 g, 99% over 2 steps). LCMS(ES+): m/z=446 [M+H].

Workup

  1. concentrationthen concentrate under reduced pressure to a white solid
  2. dissolutionDissolve the solid in MeOH
  3. washload onto a 20 g Varian SCX column, rinsing with additional MeOH
  4. washElute the free base with 1:1 2 M ammonia in MeOH
  5. concentrationConcentrate the solution under reduced pressure
  6. customto give a white solid (1.21 g, 99% over 2 steps)

Sources & evidence

ORD record
ord-adc5ea69b8084753a856298e5177121d
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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