Hydrochloric Acid → HCID 66665331, compound

HRID 872348Notes

Reaction equation

HRID 872348 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[N:25]=[C:24]([O:26][CH2:27][CH2:28][N:29]5[C:37](=[O:38])[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[C:30]5=[O:39])[CH:23]=[CH:22][N:21]4[C:40]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl.[OH-].[Na+]>CO.C(Cl)Cl.O1CCOCC1>[NH2:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[N:25]=[C:24]([O:26][CH2:27][CH2:28][N:29]5[C:37](=[O:38])[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[C:30]5=[O:39])[CH:23]=[CH:22][N:21]4[C:40]=3[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68082624HCID 68082624, compound

Product 1

HCID 66665331HCID 66665331, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

[1-(4-{7-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxy]-3-phenyl-imidazo[1,2-a]pyrimidin-2-yl}-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester (530 mg) was dissolved in methanol/DCM (1.3 mL/2.1 mL), treated with HCl in dioxane (4.08 mL of a 4M solution) and the mixture stirred overnight at rt. The reaction mixture was poured onto ice, made alkaline with 2N aqueous sodium hydroxide and extracted with EtOAc. The combined organic phases were washed with saturated aqueous sodium chloride, dried and concentrated in vacuo to give the crude title product as a yellow oil. Purification was achieved by trituration at 0° C. with diisopropyl ether. The resulting precipitate was filtered and dried to give the title compound as a solid (390 mg).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with EtOAc
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give the crude title product as a yellow oil
  7. customPurification
  8. customwas achieved by trituration at 0° C. with diisopropyl ether
  9. filtrationThe resulting precipitate was filtered
  10. customdried

Sources & evidence

ORD record
ord-e02a2213527e44d8aeb49e5b9debb95e
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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