(3-Fluoropyrrolidin-3-yl)methanamine → 6-(3-(Aminomethyl)-3-fluoropyrrolidin-1-yl)-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 525719Notes

Reaction equation

HRID 525719 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][C:34]1([CH2:39][NH2:40])[CH2:38][CH2:37][NH:36][CH2:35]1>>[NH2:40][CH2:39][C:34]1([F:33])[CH2:38][CH2:37][N:36]([C:2]2[C:21]([C:22]3[NH:26][N:25]=[CH:24][CH:23]=3)=[CH:20][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=3)=[O:7])=[CH:4][N:3]=2)[CH2:35]1

Participants

3

Reactant 2

HCID 19382172(3-Fluoropyrrolidin-3-yl)methanamineHCID 867026376-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide

Product 1

HCID 899073576-(3-(Aminomethyl)-3-fluoropyrrolidin-1-yl)-N-(4-(chlorodifluoromethoxy)phenyl)-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 (3-fluoropyrrolidin-3-yl)methanamine to afford an off-white powder. HPLC (Condition 4) tR=4.3 min, UPLC-MS (Condition 3) tR=0.80 min, m/z=481 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.92-2.10 (m, 2H) 3.03 (d, J=19.94 Hz, 2H) 3.11-3.67 (m, 6H) 6.41 (br. s, 1H) 7.31 (d, J=8.60 Hz, 2H) 7.79-7.91 (m, 3H) 8.08 (d, J=1.56 Hz, 1H) 8.73 (br. s, 1H) 10.23 (s, 1H) 12.90-13.16 (m, 1H).

Workup

  1. customto afford an off-white powder

Sources & evidence

ORD record
ord-25457dc6b8ed4d7aa3ac88ee1794e03a
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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