(3R)-piperidin-3-ol hydrochloride → HCID 89908381, compound

HRID 525764Notes

Reaction equation

HRID 525764 reaction equation
Cl[C:2]1[C:21]([C:22]2[N:26](C3CCCCO3)[N:25]=[CH:24][CH:23]=2)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.Cl.[NH:34]1[CH2:39][CH2:38][CH2:37][C@@H:36]([OH:40])[CH2:35]1>>[Cl:19][C:16]([F:18])([F:17])[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:20]=[C:21]([C:22]3[NH:26][N:25]=[CH:24][CH:23]=3)[C:2]([N:34]3[CH2:39][CH2:38][CH2:37][C@@H:36]([OH:40])[CH2:35]3)=[N:3][CH:4]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 2759333(3R)-piperidin-3-ol hydrochlorideHCID 867026376-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide

Product 1

HCID 89908381HCID 89908381, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 85 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide (Stage 48.2) and (R)-piperidin-3-ol hydrochloride and was obtained as a white solid. UPLC-MS (Condition 3) tR=0.99 min, m/z=464.1[M+H]+, m/z=508.1[M+formic acid-H]−; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.35 (m, 1H) 1.37-1.52 (m, 1H) 1.56-1.69 (m, 1H) 1.79-1.93 (m, 1H) 2.52-2.62 (m, 1H) 2.65-2.79 (m, 1H) 3.43 (d, J=12.72 Hz, 1H) 3.50-3.61 (m, 1H) 3.65 (d, J=12.23 Hz, 1H) 4.76 (d, J=4.52 Hz, 1H) 6.55-6.67 (m, 1H) 7.34 (d, J=8.93 Hz, 2H) 7.52-7.86 (m, 1H) 7.88 (d, J=9.17 Hz, 2H) 8.14-8.36 (m, 1H) 8.72 (d, J=2.32 Hz, 1H) 10.32-10.44 (m, 1H) 12.96-13.18 (m, 1H).

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-7f374fd1bd5c4b1fab803a76f93d087e
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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