Imidazole → HCID 18186485, compound

HRID 1357525Notes

Reaction equation

HRID 1357525 reaction equation
[NH:1]([C:8]1[C:13]([CH2:14]OCC)=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([OH:32])[CH2:28][N:29]([CH3:31])[CH3:30])=[CH:21][CH:20]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1>>[NH:1]([C:8]1[C:13]([CH2:14][N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([OH:32])[CH2:28][N:29]([CH3:31])[CH3:30])=[CH:21][CH:20]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 795ImidazoleHCID 11774967HCID 11774967, compound

Product 1

HCID 18186485HCID 18186485, compoundYield 25%

Procedure

Using an analogous method to that described in Example 105, but starting from 4-anilino-5-(ethoxymethyl)-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine (Example 86) and imidazole, the product was obtained in 25% yield. NMR: 2.18 (s, 6H), 2.2-2.45 (m, 2H), 3.75-3.9 (m, 3H), 4.76 (br s, 1H), 5.20 (s, 2H), 6.75 (d, 2H), 6.89 (d, 1H), 7.08 (t, 1H), 7.20 (d, 1H), 7.32 (dd, 2H), 7.50 (d, 2H), 7.61 (d, 2H), 7.78 (s, 1H), 7.96 (s, 1H), 8.54 (s, 1H), 9.00 (s, 1H); MS (MH+): 460.4.

Workup

  1. customthe product was obtained in 25% yield

Sources & evidence

ORD record
ord-c69cd2825ee7451380c82fca87156c2f
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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