D-Lactic Acid → (2r)-n-{(2r)-2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]propyl}-2-hydroxy-n-methylpropanamide

HRID 1864326Notes

Reaction equation

HRID 1864326 reaction equation
[C:1]([OH:6])(=O)[C@@H:2]([CH3:4])[OH:3].[Cl:7][C:8]1[CH:9]=[C:10]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[O:33][C@H:34]([CH3:38])[CH2:35][NH:36][CH3:37])[N:26]=[CH:25][N:24]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>>[Cl:7][C:8]1[CH:9]=[C:10]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[O:33][C@H:34]([CH3:38])[CH2:35][N:36]([CH3:37])[C:1](=[O:6])[C@H:2]([OH:3])[CH3:4])[N:26]=[CH:25][N:24]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

3

Reactant 2

HCID 61503D-Lactic AcidHCID 69055531N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(1R)-1-methyl-2-(methylamino)ethoxy]quinazolin-4-amine

Product 1

HCID 57974343(2r)-n-{(2r)-2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]propyl}-2-hydroxy-n-methylpropanamideYield 26%

Procedure

The procedure described in Example 1 was repeated using D-(−)-lactic acid and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(1R)-1-methyl-2-(methylamino)ethoxy]quinazolin-4-amine (obtained as described in Example 2.3, preparation of starting materials) to give the title compound as a white solid in 26% yield; NMR spectrum (DMSO-d6 373K) 1.15 (d, 3H), 1.44 (d, 3H), 2.97 (s, 3H), 3.16 (m, 1H), 4.05 (dd, 1H), 4.43 (m, 1H), 5.16 (m, 1H), 5.27 (s, 2H), 7.23 (m, 2H), 7.35 (m, 2H), 7.59 (m, 2H), 7.70 (t, 1H), 7.84 (dt, 1H), 8.09 (d, 1H), 8.47 (s, 1H), 8.59 (d, 1H), 9.90 (s, 1H); Mass spectrum MH+ 522.

Sources & evidence

ORD record
ord-41356762058d4f9cb0bbf652717f40b3
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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