HCID 66719111, compound → HCID 66823557, compound

HRID 2362172Notes

Reaction equation

HRID 2362172 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20]N(C)C)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[N:32]1[N:33]=[C:34]([NH2:38])[NH:35][C:36]=1[NH2:37]>C(O)(=O)C.C(O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][N:32]4[N:33]=[C:34]([NH2:38])[N:35]=[C:36]4[N:37]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 2

HCID 66719111HCID 66719111, compoundHCID 178509197HCID 178509197, compound

Product 1

HCID 66823557HCID 66823557, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 (250 mg, 0.59 mmol) and 4H-[1,2,4]Triazole-3,5-diamine (58.91 mg, 0.59 mmol) in acetic acid (0.4 mL) and ethanol (1.6 mL) was heated under reflux for 6 hours. After cooling, the mixture was diluted with 15 mL of DCM, the combined organic phase was washed with NaHCO3 aq. and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 6-1. MS (ESI) m/e (M+H+) 457.3

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. washthe combined organic phase was washed with NaHCO3 aq. and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by prep.TLC
  8. customto give 6-1

Sources & evidence

ORD record
ord-24f6de24c67449ccb82af53f6132368b
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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