Glycolic Acid → HCID 57794548, compound

HRID 2099376Notes

Reaction equation

HRID 2099376 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:5]([F:30])=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][C@H:24]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]4)=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1.[C:31](O)(=[O:34])[CH2:32][OH:33]>>[Cl:3][C:4]1[C:5]([F:30])=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][C@H:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:32](=[O:33])[CH2:31][OH:34])[CH2:25]3)=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 68908613HCID 68908613, compound

Product 1

HCID 57794548HCID 57794548, compoundYield 43.4%

Procedure

Using an analogous procedure to that described in Example 5 N-(3-chloro-2-fluorophenyl)-6-methoxy-7-[(3S)-piperidin-3-yloxy]quinazolin-4-amine dihydrochloride (250 mg) was coupled with glycolic acid (0.045 g). The resulting product was purified by flash column chromatography eluting with methanol (3%) and methylene chloride (97%) to give a foam. This was re-precipitated by stirring in diethyl ether (20 ml) to give the title product as a white solid (0.105 g); 1H NMR Spectrum: (DMSO d6 373K) 1.59 (m, 1H), 1.87 (m, 2H), 2.09 (m, 1H), 3.40-3.60 (m, 4H), 3.86 (m, 1H), 3.98 (s, 3H), 4.044.18 (m, 2H), 4.66 (m, 1H), 7.24 (m, 1H), 7.31 (s, 1H), 7.40 (m, 1H), 7.60 (m, 1H), 7.80 (s, 1H), 8.38 (s, 1H), 9.30 (br s, 1H); Mass Spectrum: (M+H)+ 461.

Workup

  1. customThe resulting product was purified by flash column chromatography
  2. washeluting with methanol (3%) and methylene chloride (97%)
  3. customto give a foam
  4. customThis was re-precipitated

Sources & evidence

ORD record
ord-7ea37d45502f4f7b8b79eafe0fd5552b
Source dataset
uspto-grants-2009_08
Patent number
US07569577B2

Reaction notes

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