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

HRID 535948Notes

Reaction equation

HRID 535948 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13](C2C=CC=CC=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].[C:29](C1N2CCNCC2=C(C(N[C@@H](C(C)(C)C)C(NC)=O)=O)N=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:29]([C:13]1[N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][C:15]2=[C:11]([C:9]([NH:8][C@@H:3]([C:2]([CH3:1])([CH3:28])[CH3:27])[C:4]([NH:6][CH3:7])=[O:5])=[O:10])[N:12]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 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-carboxamideHCID 57635545(S)-3-benzoyl-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide

Product 1

HCID 57635244(S)-3-benzoyl-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-7-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide

Procedure

Compound 289 was synthesized in the same manner as described above for Compound 48 in Example 5 except that 25C was used in place of Compound 2. 1H-NMR (400 MHz, CD3OD) δ: 1.04 (s, 9H), 2.55 (s, 3H), 2.75 (d, 3H), 2.93 (t, 2H), 4.03 (d, 2H), 4.35 (d, 1H), 4.56 (t, 2H), 7.53 (t, 2H), 7.64 (m 1H), 7.86 (d, 1H), 8.19 (m, 1H), 8.31 (d, 2H); LCMS (+ESI) m/z 412.1 [M+H]+.

Sources & evidence

ORD record
ord-7e87c53e468b4861ad98154044a7ee19
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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