1H-Pyrazol-3-amine, 5-methyl- → (S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(5-methyl-1H-pyrazol-3-ylamino)-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

HRID 242500Notes

Reaction equation

C(CCN[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.[NH2:33][C:34]1[CH:38]=[C:37]([CH3:39])[NH:36][N:35]=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]([CH3:9])([CH3:10])[CH3:11])[C:6]([NH:33][C:34]3[CH:38]=[C:37]([CH3:39])[NH:36][N:35]=3)=[O:32])=[O:14])[N:16]=2)[CH:29]=[CH:28][C:27]=1[F:30]

Participants

Reactant 2

HCID 931461H-Pyrazol-3-amine, 5-methyl-

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 46862251(S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(5-methyl-1H-pyrazol-3-ylamino)-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

Procedure

Compound 105 was prepared by the procedure described for the synthesis of compound 104 by replacing 2-cyanoethylamine with 3-amino-5-methylpyrazole. LCMS (+ESI) m/z=473.3 [M+H]+. 1H NMR (CDCl3) δ 8.15 (d, J=9.8 Hz, 1H), 7.50-7.56 (m, 1H), 7.28-7.30 (m, 1H), 7.22-7.27 (m, 1H), 5.84 (d, J=9.9 Hz, 1H), 5.48 (s, 2H), 4.82 (s, 2H), 3.93 (t, J=5.6 Hz, 2H), 3.18 (t, J=4.8 Hz, 2H), 2.17 (s, 3H), 1.11 (s, 9H).

Sources & evidence

ORD record: ord-9cc6de03937b43e9b10fe6e8635d764f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653127B2

Reaction notes

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