N-Methylaminoethanol → 2-Chloro-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol

HRID 1864196Notes

Reaction equation

HRID 1864196 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3F)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:20].CNC(O)C.CC1C=C(NC2C3C(=CC=CC=3[O:44][CH2:45][CH2:46][NH:47][CH3:48])N=CN=2)C=CC=1O>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:44][CH2:45][CH2:46][NH:47][CH3:48])[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:20]

Participants

4

Reactant 3

HCID 5247031N-MethylaminoethanolHCID 574449782-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenolHCID 690540072-Methyl-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol

Product 1

HCID 690575902-Chloro-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenolYield 96%

Procedure

2-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol was reacted with N-methylaminoethanol using an analogous process to that described in Example 3 for the preparation of 2-methyl-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol, to give 2-Chloro-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol in 96% yield; NMR spectrum (DMSO-d6) 2.41 (s, 3H), 3.05 (t, 2H), 4.36 (t, 2H), 6.97 (d, 1H), 7.12 (d, 1H), 7.31 (d, 1H), 7.63 (1H, dd), 7.70 (t, 1H), 7.96 (s, 1H), 8.47 (s, 1H) 10.47 (bs, 1H); Mass spectrum MH+ 345.

Sources & evidence

ORD record
ord-fcbbf74f408b4a1aa969c19ee50c22e2
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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