1-(2,2-Difluoroethyl)piperazine → N-(4-(Chlorodifluoromethoxy)phenyl)-6-(4-(2,2-difluoroethyl)piperazin-1-yl)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 525726

Reaction equation

HRID 525726 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.[F:33][CH:34]([F:42])[CH2:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[Cl:19][C:16]([F:17])([F:18])[O:15][C:12]1[CH:11]=[CH:10][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:39]3[CH2:40][CH2:41][N:36]([CH2:35][CH:34]([F:42])[F:33])[CH2:37][CH2:38]3)=[N:3][CH:4]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 196227971-(2,2-Difluoroethyl)piperazineHCID 867026376-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide

Product 1

HCID 118045557N-(4-(Chlorodifluoromethoxy)phenyl)-6-(4-(2,2-difluoroethyl)piperazin-1-yl)-5-(1H-pyrazol-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 33 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide (Stage 48.2) and 1-(2,2-difluoroethyl)piperazine to afford an off-white powder. HPLC (Condition 4) tR=4.72 min, UPLC-MS (Condition 3) tR=1.05 min, m/z=513 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.57 (br. s, 4H) 2.73 (td, J=15.64, 3.91 Hz, 2H) 3.09-3.22 (m, 4H) 6.13 (s, 1H) 6.67 (br. s, 1H) 7.33 (d, J=8.60 Hz, 2H) 7.86 (d, J=8.99 Hz, 3H) 8.33 (br. s, 1H) 8.73 (s, 1H) 10.40 (br. s, 1H) 12.98-13.22 (m, 1H).

Workup

  1. customto afford an off-white powder

Sources & evidence

ORD record
ord-62e8d5aac24b4a06ae30c49f588cc726
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Linked notes

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