(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-(3,4-difluorophenyl)-N-(1-(2-hydroxyethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-4,5-dihydropyrano[3,4-c]pyrazole-1(7H)-carboxamide

HRID 242495Notes

Reaction equation

HRID 242495 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[CH2:29]OC[CH2:26][C:11]=3[N:12]([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:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].FC1C=C(C2C3C[CH2:45][O:44]CC=3NN=2)C=CC=1F.N[C@@H](C(C)(C)C)[C:49](NCCO)=[O:50]>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[CH2:29][CH2:45][O:44][CH2:26][C:11]=3[N:12]([C:14]([NH:16][C@@H:17]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:18]([NH:20][CH2:21][CH2:49][OH:50])=[O:19])=[O:15])[N:13]=2)[CH:5]=[CH:6][C:7]=1[F:8]

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 593453523-(3,4-Difluorophenyl)-1,4,5,7-tetrahydropyrano[3,4-c]pyrazole

Product 1

HCID 46830663(S)-3-(3,4-difluorophenyl)-N-(1-(2-hydroxyethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-4,5-dihydropyrano[3,4-c]pyrazole-1(7H)-carboxamide

Procedure

Compound 95 was prepared according to the procedure for the synthesis of compound 28 by replacing intermediate 16 with intermediate 16B, and replacing tert-leucine methylamide with intermediate 23. LCMS (+ESI) m/z=437.4 [M+H]+. 1H NMR (CDCl3) δ 7.84 (d, J=9.2 Hz, 1H), 7.59-7.64 (m, 1H), 7.50 (br, 1H), 7.22 (q, J=9.0 Hz, 1H), 4.99 (d, J=8.1 Hz, 2H), 4.20 (d, J=9.3 Hz, 1H), 3.85-3.94 (m, 2H), 3.72 (s, 2H), 3.43 (m, 2H), 2.80 (br, 2H), 1.06 (s, 9H). Purity: 96%.

Sources & evidence

ORD record
ord-91a21388793e4ad89f1bde894f578e9b
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Reaction notes

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