(2R)-2-(Methylamino)propan-1-ol → HCID 69057495, compound

HRID 1864318Notes

Reaction equation

HRID 1864318 reaction equation
[CH3:1][NH:2][C@H:3]([CH3:6])[CH2:4][OH:5].F[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=1)=[N:11][CH:12]=[N:13]2>>[CH3:26][C:21]1[CH:20]=[C:19]([NH:18][C:10]2[C:9]3[C:14](=[CH:15][CH:16]=[CH:17][C:8]=3[O:5][CH2:4][C@H:3]([NH:2][CH3:1])[CH3:6])[N:13]=[CH:12][N:11]=2)[CH:24]=[CH:23][C:22]=1[OH:25]

Participants

3

Reactant 2

HCID 12695787(2R)-2-(Methylamino)propan-1-olHCID 574449792-Methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 69057495HCID 69057495, compoundYield 80%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using (2R)-2-(methylamino)propan-1-ol (obtained as described in Becker et al., J. Chem. Soc. 1957, 858) and 4-[(5-fluoroquinazolin-4-yl)amino]-2-methylphenol (obtained as described in Example 3, preparation of starting materials) to give 2-methyl-4-[(5-{[(2R)-2-(methylamino)propyl]oxy}quinazolin-4-yl)amino]phenol as a brown solid in 80% yield; NMR spectrum (DMSO-d6) 1.16 (d, 3H), 2.14 (s, 3H), 2.34 (s, 3H), 3.04 (m, 1H), 3.24 (bs, 1H), 4.08 (dd, 1H), 4.25 (dd, 1H), 6.76 (d, 1H), 7.06 (d, 1H), 7.26 (d, 1H), 7.47 (d, 1H), 7.53 (dd, 1H), 7.65 (t, 1H), 8.39 (s, 1H), 9.17 (s, 1H), 10.37 (s, 1H); Mass spectrum MH+ 339.

Workup

  1. customThe procedure described in Example 3 (preparation of starting materials)

Sources & evidence

ORD record
ord-84b203556bd94638a2ec50df121a6854
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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