Glycolic Acid → HCID 57974290, compound

HRID 1864211Notes

Reaction equation

HRID 1864211 reaction equation
[C:1]([OH:5])(=O)[CH2:2][OH:3].[CH2:6]([NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[C:26]([Cl:38])[CH:25]=1)=[N:16][CH:17]=[N:18]2)[CH:7]=[CH2:8]>>[CH2:6]([N:9]([CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[C:26]([Cl:38])[CH:25]=1)=[N:16][CH:17]=[N:18]2)[C:1](=[O:5])[CH2:2][OH:3])[CH:7]=[CH2:8]

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 690594755-[2-(allylamino)ethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

Product 1

HCID 57974290HCID 57974290, compoundYield 24%

Procedure

The procedure described in Example 1 was repeated using glycolic acid and 5-[2-(allylamino)ethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 11, preparation of starting materials) to give the title compound in 24% yield; NMR spectrum (DMSO-d6) 3.79-4.19 (m, 6H), 4.38-4.63 (m, 3H), 5.06-5.19 (m, 2H), 5.31 (s, 2H), 5.69-5.90 (m, 1H), 7.16 (d, 1H), 7.25 (d, 1H), 7.33-7.39 (m, 2H), 7.56-7.63 (m, 2H), 7.70-7.76 (m, 1H), 7.86-7.91 (m, 1H), 7.98 (s, 1H), 8.45 (s, 1H), 8.61 (d, 1H), 9.80 (s, 1H); Mass spectrum MH+ 520.

Sources & evidence

ORD record
ord-9804d00c81c64d96818ed90e85c45847
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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