2-Hydroxy-gamma-butyrolactone, (2S)- → (2S)-2,4-Dihydroxy-N-((2R)-2-{[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)quinazolin-5-yl]oxy}propyl)butanamide

HRID 1864339Notes

Reaction equation

HRID 1864339 reaction equation
[NH2:1][CH2:2][C@@H:3]([CH3:31])[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[C:18]([CH3:30])[CH:17]=1)=[N:8][CH:9]=[N:10]2.[OH:32][C@H:33]1[CH2:38][CH2:37][O:36][C:34]1=[O:35]>>[OH:32][C@@H:33]([CH2:38][CH2:37][OH:36])[C:34]([NH:1][CH2:2][C@H:3]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[C:18]([CH3:30])[CH:17]=1)=[N:8][CH:9]=[N:10]2)[CH3:31])=[O:35]

Participants

3

Reactant 2

HCID 3578532-Hydroxy-gamma-butyrolactone, (2S)-HCID 690586035-[(1R)-2-amino-1-methylethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine

Product 1

HCID 57974365(2S)-2,4-Dihydroxy-N-((2R)-2-{[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)quinazolin-5-yl]oxy}propyl)butanamideYield 53%

Procedure

The procedure described in Example 63 was repeated using 5-[(1R)-2-amino-1-methylethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine and (S)-α-hydroxybutyrolactone to give the title compound in 53% yield as a solid; NMR Spectrum: (CDCl3) 1.55 (d, 3H), 1.79 (m, 1H), 2.05 (m, 1H), 2.26 (s, 3H), 2.49 (s, 3H), 3.90-3.65 (m, 4H), 4.21 (dd, 1H), 4.94 (m, 1H), 6.96 (m, 2H), 7.11 (d, 1H), 7.23 (dd, 1H), 7.39 (d, 1H), 7.43 (m, 1H), 7.60-7.52 (m, 2H), 7.69 (s, 1H), 8.00 (s, 1H), 8.55 (s, 1H); Mass spectrum: MH+ 518.

Sources & evidence

ORD record
ord-66cb157fd295429eb142ef55659bb7d0
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

Loading…