(2S)-2-Amino-N,3,3-trimethylbutanamide → (S)-tert-butyl 3-bromo-1-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate

HRID 535921

Reaction equation

HRID 535921 reaction equation
CC(C)(C)[C@H](NC(C1N=C(C2C=CC=CC=2)N2CCNCC=12)=O)C(NC)=O.[CH3:28][NH:29][C:30](=[O:37])[C@H:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[NH2:32].[Br:38][C:39]1[N:43]2[CH2:44][CH2:45][N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:47][C:42]2=[C:41]([C:55](O)=[O:56])[N:40]=1>>[Br:38][C:39]1[N:43]2[CH2:44][CH2:45][N:46]([C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49])[CH2:47][C:42]2=[C:41]([C:55](=[O:56])[NH:32][C@@H:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:30]([NH:29][CH3:28])=[O:37])[N:40]=1

Participants

4

Reactant 3

HCID 445856(2S)-2-Amino-N,3,3-trimethylbutanamideHCID 25132789(S)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamideHCID 576354283-bromo-7-[(tert-butoxy)carbonyl]-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylic acid

Product 1

HCID 57635359(S)-tert-butyl 3-bromo-1-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate

Procedure

Additional compounds 22-29 were synthesized by the same procedure as described above (Examples 1 and 2) for Compound 2 except that in Example 1, alternative amines were used in place of L-tert-Leucine methylamide in the reaction with intermediate Intermediate 1I to form intermediate Intermediate 1J. For example, Compound 22 was synthesized in the same manner as Compound 2 except that (S)-2-amino-3,3-dimethylbutan-1-ol was used in place of L-tert-Leucine methylamide. Compound 23 was synthesized in the same manner as Compound 2 except that (R)-2-amino-3,3-dimethylbutan-1-ol was used in place of L-tert-Leucine methylamide. These resulting intermediates were deprotected with TFA, as described in Example 2, to form additional Compounds 22-29.

Sources & evidence

ORD record
ord-3f8f4c52b8164e35a94f91d270a7906c
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Linked notes

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