Triethylamine → HCID 66744380, compound

HRID 1959454Notes

Reaction equation

HRID 1959454 reaction equation
[C:1]([O:5][C:6]([N:8]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:9]1[C:10]([C:16]2[O:20][C:19]([C:21]3[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]=3)=[N:18][N:17]=2)=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:44]1[C:48]2([CH2:52][CH2:51][NH:50][CH2:49]2)[CH2:47][N:46]([C:53](=[O:56])[CH2:54][CH3:55])[CH2:45]1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:9]1[C:10]([C:16]2[O:20][C:19]([C:21]3[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]=3)=[N:18][N:17]=2)=[N:11][C:12]([N:50]2[CH2:51][CH2:52][C:48]3([CH2:44][CH2:45][N:46]([C:53](=[O:56])[CH2:54][CH3:55])[CH2:47]3)[CH2:49]2)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59472131HCID 59472131, compoundHCID 66744467HCID 66744467, compound

Product 1

HCID 66744380HCID 66744380, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-bromo-pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (153 mg, 0.23 mmol) and 1-(3,7-diazaspiro[4.4]nonan-3-yl)propan-1-one (101 mg, 0.46 mmol) in DMF (2 mL) was added Et3N (70 mg, 97 μL, 0.70 mmol). The reaction vessel was sealed and heated at 90° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with brine (2×). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using 0-60% EtOAc in DCM to yield tert-butyl N-[[4-[5-[3[bis(tert-butoxycarbonyl)amino]-6-(3-propanoyl-3,7-diazaspiro[4.4]nonan-7-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (133 mg, 75%). LC/MS m/z 763.9 [M+H]+.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with brine (2×)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cbc39a911d3f481084d9ae14c7a12fa6
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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