Glycolic Acid → HCID 69056760, compound

HRID 1864302Notes

Reaction equation

[C:1]([OH:5])(=O)[CH2:2][OH:3].[NH2:6][CH2:7][C@@H:8]([CH3:29])[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]([OH:27])=[C:23]([CH3:28])[CH:22]=1)=[N:13][CH:14]=[N:15]2>>[OH:3][CH2:2][C:1]([NH:6][CH2:7][C@H:8]([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]([OH:27])=[C:23]([CH3:28])[CH:22]=1)=[N:13][CH:14]=[N:15]2)[CH3:29])=[O:5]

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 57501947HCID 57501947, compound

Product 1

HCID 69056760HCID 69056760, compoundYield 59%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using glycolic acid and 4-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-methylphenol to give 2-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide as a dark brown solid in 59% yield; NMR spectrum (DMSO-d6) 1.41 (d, 3H), 2.17 (s, 3H), 3.43 (dt, 1H), 3.75 (dt, 1H), 3.78 (s, 2H), 5.01 (m, 1H), 6.84 (d, 1H), 7.30 (d, 1H), 7.32 (dd, 1H), 7.39 (d, 1H), 7.46 (d, 1H), 7.95 (t, 1H), 8.22 (t, 1H), 8.75 (s, 1H), 9.54 (d, 1H), 10.78 (s, 1H); Mass spectrum MH+ 383.

Workup

customThe procedure described in Example 3 (preparation of starting materials)

Sources & evidence

ORD record: ord-e9d98a86a6f34047b2cdd69d8ccd7bdc
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

Loading…