Water → HCID 66745843, compound

HRID 1959471Notes

Reaction equation

HRID 1959471 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][C:7]([C:10]2[N:15]=[C:14]([C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:23][CH:22]=4)=[N:18][N:17]=3)[C:13]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[N:12][CH:11]=2)=[CH:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH:4]1[CH2:9][CH2:8][C:7]([C:10]2[N:15]=[C:14]([C:16]3[O:20][C:19]([C:21]4[CH:22]=[CH:23][C:24]([CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[CH:25][CH:26]=4)=[N:18][N:17]=3)[C:13]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[N:12][CH:11]=2)=[CH:6][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86662089HCID 86662089, compound

Product 1

HCID 66745843HCID 66745843, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-[[4-[5-[6-(4-azidocyclohexen-1-yl)-3-(tert-butoxycarbonylamino)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (103 mg, 0.17 mmol) in anhydrous THF (1.5 mL) was added triphenylphosphine (67 mg, 0.26 mmol) and the reaction mixture was stirred at room temperature for 1 h. Water (61 μL, 3.41 mmol) was added after 1 h, and the reaction mixture was heated at 65° C. for 3 h. The reaction mixture was allowed to cool to room temperature and was partitioned between EtOAc/aqueous brine. The layers were separated and the aqueous layer was extracted once more with EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated to dryness. The crude material was purified by silica gel column chromatography using 20% MeOH in EtOAc to yield tert-butyl N-[[4-[5-[6-(4-aminocyclohexen-1-yl)-3-(tert-butoxycarbonylamino)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (21 mg, 21%). LC/MS m/z 578.3 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated at 65° C. for 3 h
  2. temperatureto cool to room temperature
  3. customwas partitioned between EtOAc/aqueous brine
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted once more with EtOAc
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ecdcca40b14496ca421c87850b1ae28
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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