1-(Isocyanatomethyl)-2-methylbenzene → HCID 22649283, compound

HRID 393236Notes

Reaction equation

HRID 393236 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][N:5]=[C:6]=[O:7].[NH2:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1>>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:25][CH2:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)[N:16]=[CH:15][N:14]=[C:13]2[NH:12][C:6]([NH:5][CH2:4][C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[CH3:1])=[O:7]

Participants

3

Reactant 2

HCID 27333861-(Isocyanatomethyl)-2-methylbenzeneHCID 222439084-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline

Product 1

HCID 22649283HCID 22649283, compound

Procedure

Using an analogous procedure to that described in Example 3, 2-methylbenzyl isocyanate was reacted with 4-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline. The resultant solid was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride, methanol and a 1% aqueous ammonium hydroxide solution as eluent. There was thus obtained the title compound; NMR Spectrum: (CDCl3) 1.39-1.56 (m, 2H), 1.84-2.04 (m, 5H), 2.29 (s, 3H), 2.39 (s, 3H), 2.9 (d, 2H), 3.92 (s, 3H), 4.03 (d, 2H), 4.66 (d, 2H), 7.21 (m, 4H), 7.34 (m, 2H), 8.6 (s, 1H), 8.74 (s, 1H), 10.44 (t, 1H); Mass Spectrum: M+H+ 450.

Workup

  1. customThe resultant solid was purified by column chromatography on silica using
  2. temperatureincreasingly polar mixtures of methylene chloride, methanol

Sources & evidence

ORD record
ord-953a85823644415b8b89b264237ecd66
Source dataset
uspto-grants-2004_10
Patent number
US06806274B1

Reaction notes

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