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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 535955
Notes
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Reaction equation

HRID 535955 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 180
Acetone
Solvent

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-41fcf31eda594e5794940166ee4e651c
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes