2-Nitroaniline → N-(2-{6-[1-Benzyl-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-ureido]-pyrimidin-4-ylamino}-phenyl)-acrylamide

HRID 58161

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])([O-])=O.[CH2:11]([N:18]([C:42]1[CH:47]=[C:46](Cl)[N:45]=[CH:44][N:43]=1)[C:19]([N:21]([C:30]1[C:35]([Cl:36])=[C:34]([O:37][CH3:38])[CH:33]=[C:32]([O:39][CH3:40])[C:31]=1[Cl:41])COCC[Si](C)(C)C)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([N:18]([C:42]1[N:43]=[CH:44][N:45]=[C:46]([NH:1][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:10][C:34](=[O:37])[CH:33]=[CH2:32])[CH:47]=1)[C:19]([NH:21][C:30]1[C:31]([Cl:41])=[C:32]([O:39][CH3:40])[CH:33]=[C:34]([O:37][CH3:38])[C:35]=1[Cl:36])=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 69462-Nitroaniline

HCID 1317369791-Benzyl-1-(6-chloro-pyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-urea

Product 1

HCID 118029151N-(2-{6-[1-Benzyl-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-ureido]-pyrimidin-4-ylamino}-phenyl)-acrylamideYield 20%

Procedure

The compound was synthesized following the approach outlined in Procedure 2G (Example 123), substituting 2-nitro-phenylamine and 1-benzyl-1-(6-chloro-pyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-urea (preparation shown below) in step (d) to afford the title compound (26 mg, yield: 20% over five steps). 1H NMR (300 MHz, DMSO-d6) δ 12.27 (s, 1H), 9.68 (s, 1H), 8.90 (s, 1H), 8.39 (s, 1H), 7.69 (d, 1H), 7.33-7.19 (m, 6H), 6.92 (s, 1H), 6.45 (dd, 1H), 6.24 (d, 1H), 6.18 (s, 1H), 5.74 (d, 1H), 5.07 (s, 2H), 3.95 (s, 6H); MS (ESI): 593 [M+H]+.

Workup

customThe compound was synthesized

Sources & evidence

ORD record: ord-be4d1eff34b84565a5260e0af1b031b5
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434697B2

Linked notes

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