3-Bromopyridine → 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-[(3R)-1-(pyridazin-4-yl)pyrrolidin-3-yl]thiophene-2-carboxamide

HRID 873574Notes

Reaction equation

HRID 873574 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[S:21][C:20]([C:22]([NH:24][C@@H:25]3[CH2:29][CH2:28][NH:27][CH2:26]3)=[O:23])=[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[S:21][C:20]([C:22]([NH:24][C@@H:25]3[CH2:29][CH2:28][N:27]([C:7]4[CH:2]=[CH:3][N:4]=[N:30][CH:6]=4)[CH2:26]3)=[O:23])=[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 86702054(R)-5-(1-isobutyl-1H-pyrazol-4-yl)-N-(pyrrolidin-3-yl)thiophene-2-carboxamide

Product 1

HCID 867020535-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-[(3R)-1-(pyridazin-4-yl)pyrrolidin-3-yl]thiophene-2-carboxamide

Procedure

The title compound was prepared as described in Example 1C, substituting 4-bromopyridazine for 3-bromopyridine and (R)-5-(1-isobutyl-1H-pyrazol-4-yl)-N-(pyrrolidin-3-yl)thiophene-2-carboxamide for tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.85 (d, J=6.44 Hz, 6H) 1.90-2.39 (m, 3H) 3.38-3.75 (m, 4H) 3.92 (d, J=7.12 Hz, 2H) 4.43-4.71 (m, 1H) 6.62 (dd, J=6.44, 3.05 Hz, 1H) 7.19 (d, J=3.73 Hz, 1H) 7.71 (d, J=4.07 Hz, 1H) 7.79 (s, 1H) 8.13 (s, 1H) 8.55 (dd, J=8.99, 6.95 Hz, 2H) 8.64 (d, J=2.71 Hz, 1H); MS (ESI(+)) m/e 397 (M+H)+.

Sources & evidence

ORD record
ord-ffa0e3102a924d658acf68a43f1c534d
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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