2-[(2,5-Dichloropyrimidin-4-yl)amino]benzamide → HCID 25265267, compound

HRID 2091956Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:19])[NH:17][CH3:18])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[O:8][CH3:9].Cl[C:25]1[N:30]=[C:29]([NH:31][C:32]2[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=2[C:34]([NH2:36])=[O:35])[C:28]([Cl:41])=[CH:27][N:26]=1>CC(O)C.Cl>[C:34]([C:33]1[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=1[NH:31][C:29]1[C:28]([Cl:41])=[CH:27][N:26]=[C:25]([NH:1][C:2]2[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]([C:10]3[CH:11]=[CH:12][C:13]([C:16](=[O:19])[NH:17][CH3:18])=[CH:14][CH:15]=3)=[CH:6][C:7]=2[O:8][CH3:9])[N:30]=1)(=[O:35])[NH2:36]

Participants

Conditions

Temperature: 150 °C

Procedure

To the solution of methyl 4-amino-5-methoxy-4′-(methylcarbamoyl)biphenyl-2-carboxylate (Intermediate 27, 117 mg, 0.37 mmol) and 2-(2,5-dichloropyrimidin-4-ylamino)benzamide (Intermediate 3, 316 mg, 1.12 mmol) in 3 mL of i-PrOH is added 5 drops of conc. aqueous HCl. The reaction mixture is heated at 150° C. in a microwave reactor for 30 min, followed by concentration and purification by silica gel chromatography (MeOH/DCM: 1/9) to afford methyl 4-(4-(2-carbamoylphenylamino)-5-chloropyrimidin-2-ylamino)-5-methoxy-4′-(methylcarbamoyl)biphenyl-2-carboxylate; ESMS m/z 561.2 (M+H+).

Workup

concentrationfollowed by concentration and purification by silica gel chromatography (MeOH/DCM: 1/9)

Sources & evidence

ORD record: ord-6f5516625bf349ffa18d5304a5270f83
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440681B2

Reaction notes

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