Methyl iodide → (S)-1-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-7,7-dimethyl-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-7-ium iodide

HRID 1971112Notes

Reaction equation

HRID 1971112 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5].[CH3:29][I:30]>CC(C)=O>[I-:30].[CH3:1][C:2]([CH3:28])([CH3:27])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:14]2[CH2:19][CH2:18][N+:17]([CH3:29])([CH3:20])[CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57635105(S)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-7-methyl-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide2×

Product 1

HCID 86625730(S)-1-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-7,7-dimethyl-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-7-ium iodideYield 24.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(S)—N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-7-methyl-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide (Compound 48; 0.09 g, 0.24 mmol) was dissolved in acetone (2 mL) and methyl iodide (0.038 g, 0.26 mmol) was added. The reaction mixture was stirred for 18 hours. The mixture was concentrated, ethyl acetate was added and the resulting solid was filtered, washed with cold ethyl acetate and dried under vacuum to provide the desired product, Compound 311 (0.031 g, 24%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ: 0.93 (s, 9H), 2.59 (d, 3H), 3.30 (s, 6H), 3.86 (t, 2H), 4.32 (d, 1H), 4.57 (t, 2H), 5.06 (dd, 2H), 7.54 (m, 4H), 7.82 (m, 2H), 8.17 (m, 1H); LCMS (+ESI) m/z 398.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionethyl acetate was added
  3. filtrationthe resulting solid was filtered
  4. washwashed with cold ethyl acetate
  5. customdried under vacuum

Sources & evidence

ORD record
ord-126bdc62f33c4dc79a03c3763cc34a73
Source dataset
uspto-grants-2013_04
Patent number
US08431565B2

Reaction notes

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