Glycolic Acid → HCID 69057304, compound

HRID 1864266Notes

Reaction equation

[C:1]([OH:5])(=O)[CH2:2][OH:3].[NH2:6][C@@H:7]([CH3:29])[CH2:8][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]([Cl:28])[CH:22]=1)=[N:13][CH:14]=[N:15]2>>[Cl:28][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][CH2:8][C@@H:7]([NH:6][C:1](=[O:5])[CH2:2][OH:3])[CH3:29])[N:15]=[CH:14][N:13]=2)[CH:26]=[CH:25][C:24]=1[OH:27]

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 69058749HCID 69058749, compound

Product 1

HCID 69057304HCID 69057304, compoundYield 73%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using glycolic acid and 4-[(5-{[(2S)-2-aminopropyl]oxy}quinazolin-4-yl)amino]-2-chlorophenol to give N-[(1S)-2-({4-[(3-chloro-4-hydroxyphenyl)amino]quinazolin-5-yl}oxy)-1-methylethyl]-2-hydroxyacetamide in 73% yield; Mass spectrum MH+ 403.0.

Workup

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

Sources & evidence

ORD record: ord-05032caabd3849c6b258e8cd6a42cf1e
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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