Acetic Acid → (S)-7-cyclopropyl-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide

HRID 535928Notes

Reaction equation

HRID 535928 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5].C(O[C:31]1(O[Si](C)(C)C)[CH2:33][CH2:32]1)C.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH:31]1([N:17]2[CH2:18][CH2:19][N:14]3[C:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[N:12][C:11]([C:9]([NH:8][C@@H:3]([C:2]([CH3:27])([CH3:26])[CH3:1])[C:4]([NH:6][CH3:7])=[O:5])=[O:10])=[C:15]3[CH2:16]2)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 25132789(S)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide

Product 1

HCID 57635385(S)-7-cyclopropyl-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Compound 2 (60 mg, 0.16 mmol) was dissolved in methanol and (1-ethoxycyclopropoxy)trimethylsilane (170 mg, 0.94 mmol) was added followed by sodium cyanoborohydride (46 mg, 0.73 mmol) and acetic acid (98 mg, 1.62 mmol). The reaction mixture was heated at 60° C. overnight, cooled down to room temperature, filtered and concentrated.

Workup

  1. temperaturecooled down to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e74b768ee3f4404987b13d18b08a3530
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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