(S)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide → HCID 46862780, compound

HRID 242491Notes

Reaction equation

HRID 242491 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C@H:3]([NH:8][C:9](N1C2CCN(C)CC=2C(C2C=C(F)C(F)=CC=2F)=N1)=[O:10])[C:4]([NH:6][CH3:7])=[O:5].[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([F:55])=[C:37]([C:39]2[C:43]3[N:44]([C:48](OC(C)(C)C)=O)[CH2:45][CH2:46][CH2:47][C:42]=3[NH:41][N:40]=2)[CH:38]=1.N[C@@H](C(C)(C)C)[C:58](NCCO)=[O:59]>>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([F:55])=[C:37]([C:39]2[C:43]3[N:44]([CH3:48])[CH2:45][CH2:46][CH2:47][C:42]=3[N:41]([C:9]([NH:8][C@@H:3]([C:2]([CH3:1])([CH3:30])[CH3:31])[C:4]([NH:6][CH2:7][CH2:58][OH:59])=[O:5])=[O:10])[N:40]=2)[CH:38]=1

Participants

4

Reactant 3

HCID 46863441(S)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamideHCID 58124726(S)-2-amino-N-(2-hydroxyethyl)-3,3-dimethylbutanamideHCID 59345330tert-butyl 3-(5-chloro-2-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridine-4(5H)-carboxylate

Product 1

HCID 46862780HCID 46862780, compound

Procedure

Compound 94 was prepared according to the procedure for the synthesis of compound 37 by replacing intermediate 19 with intermediate 20D, and replacing tert-leucine methylamide with intermediate 23. LCMS (+ESI) m/z=466.3 [M+H]+. 1H NMR (CDCl3) δ 7.80 (d, J=8.9 Hz, 1H), 7.62-7.65 (m, 1H), 7.32-7.37 (m, 1H), 7.10 (t, J=9.0 Hz, 1H), 4.14 (d, J=8.9 Hz, 1H), 3.71 (br, 2H), 3.42-3.46 (m, 2H), 3.02-3.06 (m, 2H), 2.96 (br, 2H), 2.41 (s, 3H), 1.92 (br, 2H), 1.06 (s, 9H). Purity: 99%.

Sources & evidence

ORD record
ord-38290ccf474341a394c22d33499cfb1e
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Reaction notes

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