2-(Aminomethyl)-5-methylpyrazine → (S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-((5-methylpyrazin-2-yl)methylamino)-1-oxobutan-2-yl)-6,7-dihydropyrano-[4,3-c]pyrazole-1(4H)-carboxamide

HRID 242501Notes

Reaction equation

[C:1]([CH2:3][CH2:4][NH:5][C:6](=[O:32])[C@@H:7]([NH:12][C:13]([N:15]1[C:19]2[CH2:20][CH2:21][O:22][CH2:23][C:18]=2[C:17]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=2)=[N:16]1)=[O:14])[C:8]([CH3:11])([CH3:10])[CH3:9])#[N:2].[NH2:33][CH2:34][C:35]1[CH:40]=NC(C)=CN=1>>[F:31][C:26]1[CH:25]=[C:24]([C:17]2[C:18]3[CH2:23][O:22][CH2:21][CH2:20][C:19]=3[N:15]([C:13]([NH:12][C@@H:7]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:6]([NH:5][CH2:4][C:3]3[CH:1]=[N:2][C:35]([CH3:40])=[CH:34][N:33]=3)=[O:32])=[O:14])[N:16]=2)[CH:29]=[CH:28][C:27]=1[F:30]

Participants

Reactant 2

HCID 27564962-(Aminomethyl)-5-methylpyrazine

HCID 46862252(S)-N-(1-(2-cyanoethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-3-(3,4-difluorophenyl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

Product 1

HCID 46862250(S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-((5-methylpyrazin-2-yl)methylamino)-1-oxobutan-2-yl)-6,7-dihydropyrano-[4,3-c]pyrazole-1(4H)-carboxamide

Procedure

Compound 106 was prepared by the procedure described for the synthesis of compound 104 by replacing 2-cyanoethylamine with 2-aminomethyl-5-methylpyrazine. LCMS (+ESI) m/z=499.3 [M+H]+. 1H NMR (CDCl3) δ 8.48 (s, 1H), 8.35 (s, 1H), 7.92 (d, J=9.4 Hz, 1H), 7.47-7.52 (m, 1H), 7.28-7.32 (m, 1H), 7.19-7.27 (m, 1H), 6.98 (br, 1H), 4.82 (s, 2H), 4.57-4.62 (m, 2H), 4.30 (d, J=10.4 Hz, 1H), 3.93 (t, J=5.4 Hz, 2H), 3.18 (br, 2H), 2.80 (s, 3H), 1.11 (s, 9H).

Sources & evidence

ORD record: ord-d23611f5ed0e46bf97af4e9e79331901
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653127B2

Reaction notes

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