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

HRID 58163Notes

Reaction equation

HRID 58163 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])([O-])=O.Cl[C:12]1[N:17]=[CH:16][N:15]=[C:14]([N:18]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[C:19]([N:21]([C:30]2[C:35]([Cl:36])=[C:34]([O:37][CH3:38])[CH:33]=[C:32]([O:39][CH3:40])[C:31]=2[Cl:41])COCC[Si](C)(C)C)=[O:20])[CH:13]=1>>[Cl:41][C:31]1[C:32]([O:39][CH3:40])=[CH:33][C:34]([O:37][CH3:38])=[C:35]([Cl:36])[C:30]=1[NH:21][C:19](=[O:20])[N:18]([C:14]1[N:15]=[CH:16][N:17]=[C:12]([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:13]=1)[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=1

Participants

3

Reactant 2

HCID 69462-NitroanilineHCID 131736980HCID 131736980, compound

Product 1

HCID 118029234N-(2-{6-[3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-pyridin-2-ylmethyl-ureido]-pyrimidin-4-ylamino}-phenyl)-acrylamideYield 13%

Procedure

The compound was synthesized following the approach outlined in Procedure 2G (Example 123), substituting 2-nitro-phenylamine and 1-(6-chloro-pyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-pyridin-2-ylmethyl-3-(2-trimethylsilanyl-ethoxymethyl)-urea (preparation shown below) in step (d) to afford the title compound (35 mg, yield: 13% over five steps). 1H NMR (300 MHz, DMSO-d6) δ 12.15 (s, 1H), 9.65 (s, 1H), 8.83 (s, 1H), 8.50 (s, 1H), 8.39 (s, 1H), 7.80 (t, 1H), 7.66 (d, 1H), 7.31-7.25 (m, 3H), 7.17 (t, 1H), 7.09 (t, 1H), 6.91 (s, 1H), 6.45 (dd, 1H), 6.39 (s, 1H), 6.23 (d, 1H), 5.74 (d, 1H), 5.17 (s, 2H), 3.94 (s, 6H); MS (ESI): 594 [M+H]+.

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-d6f27f3dbdbd41b0b6c0f8dc92705f61
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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