Glycolic Acid → HCID 57974301, compound

HRID 1864236Notes

Reaction equation

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

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 69062744HCID 69062744, compound

Product 1

HCID 57974301HCID 57974301, compoundYield 47%

Procedure

The procedure described in Example 1 was repeated using glycolic acid and 5-[(1S)-2-amino-1-methylethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 36, preparation of starting materials) to give the title compound in 47% yield; NMR spectrum (DMSO-d6) 1.20 (d, 3H), 3.41 (m, 1H), 3.74 (m, 1H), 3.78 (d, 2H), 4.92 (m, 1H), 5.29 (s, 2H), 5.48 (t, 1H), 7.23 (dd, 2H), 7.31 (d, 1H), 7.35 (m, 1H), 7.58 (m, 2H), 7.70 (t, 1H), 7.87 (td, 1H), 8.13 (d, 1H), 8.17 (t, 1H), 8.47 (s, 1H), 8.58 (d, 1H), 9.98 (s, 1H); Mass Spectrum MH+ 494.

Sources & evidence

ORD record: ord-82188ea8ee6b4556bc8e3cd291a29017
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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