Triethylamine → HCID 66745553, compound

HRID 1959472Notes

Reaction equation

HRID 1959472 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[O:18][C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:21][CH:20]=4)=[N:16][N:15]=3)[C:11]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[N:10][CH:9]=2)=[CH:4][CH2:3]1.CCN(CC)CC.[C:50](Cl)(=[O:53])[CH2:51][CH3:52]>C(Cl)Cl>[C:39]([O:38][C:36]([NH:35][C:11]1[C:12]([C:14]2[O:18][C:17]([C:19]3[CH:20]=[CH:21][C:22]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:23][CH:24]=3)=[N:16][N:15]=2)=[N:13][C:8]([C:5]2[CH2:6][CH2:7][CH:2]([NH:1][C:50](=[O:53])[CH2:51][CH3:52])[CH2:3][CH:4]=2)=[CH:9][N:10]=1)=[O:37])([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 66745843HCID 66745843, compound

Product 1

HCID 66745553HCID 66745553, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 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 (20 mg, 0.03 mmol) in anhydrous DCM (200 μL) was added Et3N (5 mg, 7 μL, 0.05 mmol) and the reaction mixture was cooled in an ice water bath. A solution of propanoyl chloride (3.843 mg, 3.625 μL, 0.04154 mmol) in DCM (0.1 mL) was added dropwise to the above reaction mixture. The reaction mixture was diluted with DCM and washed once with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using 10% MeOH in EtOAc to yield tert-butyl N-[[4-[5-[3-(tert-butoxycarbonylamino)-6-[4-(propanoylamino)cyclohexen-1-yl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (21 mg, 96%).

Workup

  1. temperaturethe reaction mixture was cooled in an ice water bath
  2. washwashed once with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1dd47af9d35048d2841a12b4e93a81c7
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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