Glycolic Acid → HCID 44442028, compound

HRID 1864244Notes

Reaction equation

HRID 1864244 reaction equation
[C:1]([OH:5])(=O)[CH2:2][OH:3].[Cl:6][C:7]1[CH:8]=[C:9]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][C:30]=3[O:32][C@@H:33]([CH3:37])[CH2:34][NH:35][CH3:36])[N:25]=[CH:24][N:23]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>>[Cl:6][C:7]1[CH:8]=[C:9]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][C:30]=3[O:32][C@@H:33]([CH3:37])[CH2:34][N:35]([CH3:36])[C:1](=[O:5])[CH2:2][OH:3])[N:25]=[CH:24][N:23]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 69058100HCID 69058100, compound

Product 1

HCID 44442028HCID 44442028, compoundYield 53%

Procedure

The procedure described in Example 1 was repeated using glycolic acid and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(1S)-1-methyl-2-(methylamino) ethoxy]quinazolin-4-amine (obtained as described for the R-antipode in Example 2.3, preparation of starting materials) to give the title compound in 53% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.96 (s, 3H), 3.36 (dd, 1H), 4.04 (d, 2H), 4.21 (m, 1H), 4.37 (t, 1H), 5.09 (m, 1H), 5.29 (s, 1H), 7.25 (m, 2H), 7.35 (m, 2H), 7.57 (d, 1H), 7.65 (dd, 1H), 7.70 (t, 1H), 7.87 (dt, 1H), 8.12 (d, 1H), 8.46 (s, 1H), 8.58 (d, 1H), 9.93 (s, 1H); Mass Spectrum MH+ 508.

Workup

  1. customobtained
  2. customas described for the R-antipode in Example 2.3, preparation of starting materials)

Sources & evidence

ORD record
ord-3c44b2b9191a41f480285da6f3d0684b
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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