5-fluoro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine → 5-{(1S)-2-[allyl(methyl)amino]-1-methylethoxy}-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine

HRID 1864337Notes

Reaction equation

HRID 1864337 reaction equation
[CH2:1]([N:4]([CH3:9])[CH2:5][C@@H:6]([OH:8])[CH3:7])[CH:2]=[CH2:3].F[C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=3)=[C:24]([CH3:36])[CH:23]=1)=[N:14][CH:15]=[N:16]2>>[CH2:1]([N:4]([CH3:9])[CH2:5][C@H:6]([CH3:7])[O:8][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=3)=[C:24]([CH3:36])[CH:23]=1)=[N:14][CH:15]=[N:16]2)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 690241975-fluoro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amineHCID 86615688(2S)-1-[allyl(methyl)amino]propan-2-ol

Product 1

HCID 690539405-{(1S)-2-[allyl(methyl)amino]-1-methylethoxy}-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amineYield 92%

Procedure

The procedure described in Example 103, preparation of starting materials, was repeated using (2S)-1-[allyl(methyl)amino]propan-2-ol (obtained as described for the R-antipode in Example 2.3, preparation of starting materials) and 5-fluoro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine (obtained as described in Example 103, preparation of starting materials) to give 5-{(1S)-2-[allyl(methyl)amino]-1-methylethoxy}-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine in 92% yield as a gum; Mass spectrum: MH+ 470.

Workup

  1. customThe procedure described in Example 103, preparation of starting materials
  2. customobtained

Sources & evidence

ORD record
ord-1117bcd657a04c1bb9fe8d20c4c7c069
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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