Glycolic Acid → HCID 11295994, compound

HRID 1864220Notes

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][CH2:33][CH2:34][NH:35][CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]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>>[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][CH2:33][CH2:34][N:35]([CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[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

Reactant 2

HCID 757Glycolic Acid

HCID 69055949HCID 69055949, compound

Product 1

HCID 11295994HCID 11295994, compoundYield 12%

Procedure

The procedure described in Example 1 was repeated using glycolic acid and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(tetrahydro-2H-pyran-4-ylamino)ethoxy]quinazolin-4-amine (obtained as described in Example 20, preparation of starting materials) to give the title compound in 12% yield; NMR spectrum (DMSO-d6) 1.53-1.69 (m, 2H), 1.77-2.07 (m, 2H), 3.34-3.42 (m, 2H), 3.73-3.92 (m, 5H), 4.14-4.25 (m, 2H), 4.31-4.54 (m, 3H), 5.31 (s, 2H), 7.21-7.29 (m, 2H), 7.32-7.40 (m, 2H), 7.57-7.63 (m, 2H), 7.70-7.76 (m, 1H), 7.86-7.91 (m, 1H), 8.03 (s, 1H), 8.47 (s, 1H), 8.61 (d, 1H), 9.99 (s, 1H); Mass spectrum MH+ 564.

Sources & evidence

ORD record: ord-46fcaf470b5a463792e6a5c87ac1a608
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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