Ethyl orthoformate → HCID 49869931, compound

HRID 571960Notes

Reaction equation

HRID 571960 reaction equation
[CH:1](OCC)(OCC)OCC.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C@H:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([N:28]3[CH:32]=[N:31][N:30]=[CH:29]3)[CH2:23]2)(=[O:20])=[O:19])=[C:14]([CH2:33][CH3:34])[CH:13]=1.[N-:35]=[N+:36]=[N-:37].[Na+]>C(O)(=O)C>[CH2:33]([C:14]1[CH:13]=[C:12]([N:11]2[CH:1]=[N:37][N:36]=[N:35]2)[CH:17]=[CH:16][C:15]=1[S:18]([NH:21][C@H:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([N:28]2[CH:29]=[N:30][N:31]=[CH:32]2)[CH2:23]1)(=[O:20])=[O:19])[CH3:34]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 67491011HCID 67491011, compound

Product 1

HCID 49869931HCID 49869931, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Triethyl orthoformate (70.0 μL, 0.420 mmol) was added to a mixture of 4a (33.0 mg, 0.094 mmol) and sodium azide (20.0 mg, 0.308 mmol) in acetic acid (1.00 mL), and the resulting mixture was heated to 90° C. After 15 h, the reaction mixture was cooled to rt, quenched with satd. aq. NaHCO3 and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% MeOH/DCM as eluent) to afford the title compound, 5a. m/z (ES) 403 (MH)+; IC50=815 nM

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customquenched with satd
  3. extractionaq. NaHCO3 and extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-e1369fb80f3a4630b223f3346c88fc46
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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