3-Bromopyridine → N-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}-1-(pyridazin-4-yl)azetidine-3-carboxamide

HRID 873569Notes

Reaction equation

HRID 873569 reaction equation
Br[C:2]1[CH:3]=[N:4]C=[CH:6][CH:7]=1.[CH2:8]([N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([CH:26]3[CH2:29][NH:28][CH2:27]3)=[O:25])=[CH:19][CH:18]=2)[CH:14]=[N:13]1)[CH:9]([CH3:11])[CH3:10].[NH:30]1CC(C(NC2C=CC(OC3CCN(C(OC(C)(C)C)=O)CC3)=CC=2)=O)C1>>[CH3:10][CH:9]([CH3:11])[CH2:8][N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([CH:26]3[CH2:27][N:28]([C:7]4[CH:2]=[CH:3][N:4]=[N:30][CH:6]=4)[CH2:29]3)=[O:25])=[CH:19][CH:18]=2)[CH:14]=[N:13]1

Participants

4

Reactant 3

HCID 122863-BromopyridineHCID 86702036Tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylateHCID 86702046N-(4-(1-isobutyl-1H-pyrazol-4-yl)phenyl)azetidine-3-carboxamide

Product 1

HCID 86702045N-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}-1-(pyridazin-4-yl)azetidine-3-carboxamide

Procedure

The title compound was prepared as described in Example 1C, substituting 4-bromopyridazine for 3-bromopyridine and N-(4-(1-isobutyl-1H-pyrazol-4-yl)phenyl)azetidine-3-carboxamide for tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.10 (s, 1H), 8.61 (d, J=6.0 Hz, 1H), 8.51 (d, J=3.0 Hz, 1H), 8.08 (s, 1H), 7.81 (s, 1H), 7.64-7.56 (m, 2H), 7.55-7.48 (m, 2H), 6.55 (dd, J=6.0, 3.0 Hz, 1H), 4.31-3.96 (m, 4H), 3.91 (d, J=7.1 Hz, 2H), 3.74 (s, 1H), 2.12 (dd, J=13.3, 6.5 Hz, 1H), 0.86 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 377 (M+H)+.

Sources & evidence

ORD record
ord-bbc66d81cbd842c9832a1ee12b3e0b4c
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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