Piperidin-4-ol → (3-(3,4-difluorophenyl)-5-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)(4-hydroxypiperidin-1-yl)methanone

HRID 242457Notes

Reaction equation

HRID 242457 reaction equation
CC(C)(C)[C@H:3]([NH:8][C:9]([N:11]1[C:19]2[CH2:18][CH2:17][N:16]([CH3:20])[CH2:15][C:14]=2[C:13]([C:21]2[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=2F)=[N:12]1)=[O:10])[C:4](NC)=O.FC1C=C(C2C3CN(C(OC(C)(C)C)=O)CCC=3NN=2)C=CC=1F.[OH:56][CH:57]1CCN[CH2:59][CH2:58]1>>[F:27][C:25]1[CH:26]=[C:21]([C:13]2[C:14]3[CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][C:19]=3[N:11]([C:9]([N:8]3[CH2:59][CH2:58][CH:57]([OH:56])[CH2:4][CH2:3]3)=[O:10])[N:12]=2)[CH:22]=[CH:23][C:24]=1[F:28]

Participants

4

Reactant 3

HCID 79341Piperidin-4-olHCID 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 59345327tert-butyl 3-(3,4-difluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate

Product 1

HCID 46863445(3-(3,4-difluorophenyl)-5-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)(4-hydroxypiperidin-1-yl)methanone

Procedure

Compound 45 was prepared according to the procedure described for the synthesis of compound 37 by replacing intermediate 19 with intermediate 15, and replacing tert-leucine methyl amide with 4-hydroxypiperidine. 1H NMR (CDCl3) δ 7.46-7.51 (m, 1H), 7.32-7.36 (m, 1H), 7.20 (q, J=8.9 Hz, 1H), 3.96-4.08 (m, 3H), 3.60 (s, 2H), 3.41-3.47 (m, 2H), 3.08 (t, J=5.6 Hz, 2H), 2.78 (t, J=5.8 Hz, 2H), 2.54 (s, 3H), 1.97-2.01 (m, 2H), 1.63-1.72 (m, 2H). LCMS (+ESI) m/z=377 [M+H]+.

Sources & evidence

ORD record
ord-a133a4d97b08442faec252ec27f4b685
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Reaction notes

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