Diisopropylethylamine → HCID 86730144, compound

HRID 1850116Notes

Reaction equation

HRID 1850116 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][CH:4]=1.[N:19]1[N:20]=[CH:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][C:23]=12.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[N:19]1[N:20]=[CH:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][CH:4]=3)[CH2:24][C:23]=12

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 179987185H,6H,7H,8H-(1,2,4)triazolo(4,3-a)pyrazineHCID 86730143HCID 86730143, compound

Product 1

HCID 86730144HCID 86730144, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-tert-butyl 1-(4-(chloromethyl)phenyl)ethylcarbamate (127 mg, 0.47 mmol), 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (91 mg, 0.56 mmol) and DIPEA (183 mg, 1.41 mmol) in DMSO (2.3 mL) was heated at 80° C. for 16 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). After separation, the aqueous phase was washed with EtOAc (2×15 mL). Combined organics were dried over Na2SO4, filtered and concentrated. The crude product was used to next step without further purification.

Workup

  1. washwashed with water (20 mL)
  2. customAfter separation
  3. washthe aqueous phase was washed with EtOAc (2×15 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was used to next step without further purification

Sources & evidence

ORD record
ord-2850fe8e3de74026ab8dacd377d29e18
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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