HCID 86702544, compound → HCID 57378749, compound

HRID 877070Notes

Reaction equation

HRID 877070 reaction equation
[CH3:1][O:2][C:3](=[O:43])/[CH:4]=[CH:5]/[C:6]1[C:14]2[C:10](=[C:11]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([C:25]5([NH:29]C(OC(C)(C)C)=O)[CH2:28][CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[C:16]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:15][N:12]3[N:13]=2)[CH:9]=[CH:8][CH:7]=1>Cl.O1CCOCC1>[CH3:1][O:2][C:3](=[O:43])/[CH:4]=[CH:5]/[C:6]1[C:14]2[C:10](=[C:11]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([C:25]5([NH2:29])[CH2:28][CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[C:16]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[CH:15][N:12]3[N:13]=2)[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 86702544HCID 86702544, compound

Product 1

HCID 57378749HCID 57378749, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

275 mg of the crude (E)-3-{2-[4-(1-tert-Butoxycarbonylaminocyclobutyl)phenyl]-3-phenylpyrimido[1,2-b]indazol-7-yl}acrylic acid methyl ester were stirred in 15 mL 4M hydrogen chloride in dioxane for 18 hours at room temperature. The solvent was evaporated and the residue was stirred with saturated sodium bicarbonate for one hour at room temperature. After addition of dichloromethane stirring was continued for another hour. The organic phase was separated and the aqueous phase was extracted once more with dichloromethane. The combined organic extracts were washed with water and brine, dried and filtrated. The solvent was evaporated and the residue purified by HPLC 35.7 mg (15.7%) of the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionAfter addition of dichloromethane stirring
  3. waitwas continued for another hour
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted once more with dichloromethane
  6. washThe combined organic extracts were washed with water and brine
  7. customdried
  8. filtrationfiltrated
  9. customThe solvent was evaporated
  10. customthe residue purified by HPLC 35.7 mg (15.7%) of the title compound

Sources & evidence

ORD record
ord-9c2b72efac5043838bdd533fde2ac8d5
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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