(S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(methyl-amino)-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide → (S)-3-(5-chloro-2-fluorophenyl)-N-(1-(2-hydroxyethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-4,5-dihydropyrano[3,4-c]pyrazole-1(7H)-carboxamide

HRID 242496

Reaction equation

HRID 242496 reaction equation
FC1C=C(C2C3COCCC=3N([C:14]([NH:16][C@@H:17]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:18]([NH:20][CH3:21])=[O:19])=[O:15])N=2)C=CC=1F.[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([F:46])=[C:35]([C:37]2[C:38]3[CH2:45][CH2:44][O:43][CH2:42][C:39]=3[NH:40][N:41]=2)[CH:36]=1.N[C@@H](C(C)(C)C)[C:49](NCCO)=[O:50]>>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([F:46])=[C:35]([C:37]2[C:38]3[CH2:45][CH2:44][O:43][CH2:42][C:39]=3[N:40]([C:14]([NH:16][C@@H:17]([C:22]([CH3:23])([CH3:24])[CH3:25])[C:18]([NH:20][CH2:21][CH2:49][OH:50])=[O:19])=[O:15])[N:41]=2)[CH:36]=1

Participants

4

Reactant 3

HCID 46834697(S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(methyl-amino)-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamideHCID 58124726(S)-2-amino-N-(2-hydroxyethyl)-3,3-dimethylbutanamideHCID 593453293-(5-Chloro-2-fluorophenyl)-1,4,5,7-tetrahydropyrano[3,4-c]pyrazole

Product 1

HCID 46830664(S)-3-(5-chloro-2-fluorophenyl)-N-(1-(2-hydroxyethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-4,5-dihydropyrano[3,4-c]pyrazole-1(7H)-carboxamide

Procedure

Compound 96 was prepared according to the procedure for the synthesis of compound 28 by replacing intermediate 16 with intermediate 16C, and replacing tert-leucine methylamide with intermediate 23. LCMS (+ESI) m/z=453.3 [M+H]+. 1H NMR (CDCl3) δ 7.82 (d, J=9.3 Hz, 1H), 7.61-7.63 (m, 1H), 7.32-7.36 (m, 1H) 7.09 (t, J=9.2 Hz, 1H), 4.99 (d, J=8.0 Hz, 2H), 4.19 (d, J=9.3 Hz, 1H), 3.78-3.88 (m, 2H), 3.69 (s, 2H), 3.43 (m, 2H), 2.63 (br, 2H), 1.06 (s, 9H). Purity: 91%.

Sources & evidence

ORD record
ord-b5f56fe59f194e85ae98fa1b39a33a6b
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Linked notes

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