Cesium carbonate → 6-(4-(4-Acetylpiperazin-1-yl)phenylamino)-4-(thiophen-2-ylmethylamino)nicotinamide
Reaction equation
Cl[C:2]1[CH:10]=[C:9]([NH:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31](=[O:33])[CH3:32])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:31]([N:28]1[CH2:27][CH2:26][N:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:2]3[CH:10]=[C:9]([NH:11][CH2:12][C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=3)=[CH:20][CH:21]=2)[CH2:30][CH2:29]1)(=[O:33])[CH3:32]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 6-chloro-4-(thiophen-2-ylmethylamino)nicotinamide (84 mg, 0.314 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (82 mg, 0.374 mmol), Cs2CO3 (200 mg, 0.613 mmol), BINAP (35 mg, 0.056 mmol) and Pd(OAc)2 (25 mg, 0.111 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 120 C for 3 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to the titled compound (12 mg). MS 451.4 (M+H); UV 200.0, 244.3 nm; t 0.485 min.
Workup
- customwas degassed with Ar
- concentrationThe mixture was concentrated in vacuo
- customThe residue was purified by HPLC to the titled compound (12 mg)
- customt 0.485 min.
Sources & evidence
- ORD record
- ord-cbedb28fa18f430c937363c4b2863dc9
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102625B2
Reaction notes
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