Cesium carbonate → 6-(4-(Dimethylcarbamoyl)phenylamino)-4-(3-(pyridine-4-yl)benzylamino)nicotinamide

HRID 513292Notes

Reaction equation

Cl[C:2]1[CH:10]=[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH:14]=2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:25][C:26]1[CH:36]=[CH:35][C:29]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:28][CH:27]=1.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.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:33][N:32]([CH3:34])[C:30]([C:29]1[CH:35]=[CH:36][C:26]([NH:25][C:2]2[CH:10]=[C:9]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:14]=3)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)=[CH:27][CH:28]=1)=[O:31]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 6-chloro-4-(3-(pyridine-4-yl)benzylamino)nicotinamide (56 mg, 0.1 mmol) in p-Dioxane (2 mL) was added 4-amino-N,N-dimethylbenzamide (41 mg, 0.244 mmol), Pd(OAc)2 (7.5 mg, 0.033 mmol), BINAP (21 mg, 0.033 mmol) and Cs2CO3 (162 mg, 0.498 mmol). After stirred at 80° C. for 15 h, it was concentrated and purified by preparative HPLC to give 6-(4-(dimethylcarbamoyl)phenylamino)-4-(3-(pyridine-4-yl)benzylamino)nicotinamide. MS found for C27H26N6O2 as (M+H)+ 467.3. UV: λ=217.6, 272.7, 294.9 nm. 1H NMR: (CD3OD) δ 8.78 (dd, J=5.2, 1.2 Hz, 2H), 8.22 (s, 1H), 8.14 (dd, J=5.6, 1.2 Hz, 2H), 7.89 (bd, J=3.6 Hz, 1H), 7.85 (bs, 1H), 7.63 (t, J=3.6 Hz, 1H), 7.54 (d, J=7.2 Hz, 1H), 7.37 (d, J=9.2 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 6.02 (s, 1H), 4.65 (s, 2H), 3.09 (s, 3H), 2.97 (s, 3H) ppm.

Workup

concentrationit was concentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-5b6a2c9f61d648b2a90173e06004e4d3
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102625B2

Reaction notes

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