1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 1-[[(2S)-1-[(Z)-1-aminoethylideneamino]oxy-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-3-phenyl-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxylate

HRID 2110207Notes

Reaction equation

HRID 2110207 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:15][C:16]([C:17]([NH:19][C@@H:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([OH:23])=[O:22])=[O:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O/[N:56]=[C:57](\[NH2:59])/[CH3:58]>CN(C=O)C.O>[NH2:59]/[C:57](=[N:56]\[O:22][C:21](=[O:23])[C@@H:20]([NH:19][C:17]([C:16]1[N:15]=[C:14]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]=12)=[O:18])[C:24]([CH3:26])([CH3:27])[CH3:25])/[CH3:58]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5487681(E)-N'-HydroxyacetimidamideHCID 57635146(S)-2-(7-(tert-butoxycarbonyl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamido)-3,3-dimethylbutanoic acid

Product 1

HCID 57635411tert-butyl 1-[[(2S)-1-[(Z)-1-aminoethylideneamino]oxy-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-3-phenyl-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Intermediate 22B (0.25 g, 0.55 mmol) was dissolved in DMF and EDCI (0.17 g, 0.87 mmol) was added, followed by HOBt (0.12 g, 0.87 mmol). The resulting mixture was stirred for 30 min and (Z)-N′-hydroxy-acetimidamide (0.06 g, 0.82 mmol) was added and the mixture was stirred overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed successively with water, 2N Na2CO3 solution and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was used in the next step without purification. LCMS (+ESI) m/z 1025.2 [2M+H]+.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed successively with water, 2N Na2CO3 solution and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was used in the next step without purification

Sources & evidence

ORD record
ord-59caf9f5bd6e400b839a74ffd3027665
Source dataset
uspto-grants-2009_04
Patent number
US07517874B2

Reaction notes

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