N,N-dimethylazetidin-3-amine → HCID 89907593, compound

HRID 525732Notes

Reaction equation

HRID 525732 reaction equation
Cl[C:2]1[C:21]([C:22]2[NH:26][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.[CH3:27][N:28]([CH3:33])[CH:29]1[CH2:32][NH:31][CH2:30]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:31]3[CH2:32][CH:29]([N:28]([CH3:33])[CH3:27])[CH2:30]3)=[N:3][CH:4]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 10351656N,N-dimethylazetidin-3-amineHCID 72201589HCID 72201589, compound

Product 1

HCID 89907593HCID 89907593, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 38 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide (Stage 48.1) and N,N-dimethylazetidin-3-amine to afford a white solid. HPLC (Condition 7) tR=5.768 min, UPLC-MS (Condition 3) tR=0.78 min, m/z=463.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.01 (s, 6H) 2.90-3.06 (m, 1H) 3.51-3.62 (m, 2H) 3.71-3.86 (m, 2H) 6.37-6.48 (m, 1H) 7.33 (d, J=8.60 Hz, 2H) 7.53-7.93 (m, J=9.4 Hz, 3H) 8.08 (d, J=2.35 Hz, 1H) 8.74 (d, J=1.95 Hz, 1H) 10.19-10.29 (m, 1H) 12.91-13.22 (m, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-bedba98c39774258babb583e932665eb
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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