Glycolic Acid → HCID 58710706, compound

HRID 1442985Notes

Reaction equation

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

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 68677219HCID 68677219, compound

Product 1

HCID 58710706HCID 58710706, compoundYield 45%

Procedure

The procedure described in Example 1 was repeated using N-(3-chloro-4-fluoro-phenyl)-7-methoxy-5-(pyrrolidin-3-ylmethoxy)quinazolin-4-amine (100 mg) and glycolic acid (21 mg) to give the title product in 45% yield; NMR spectrum (DMSO-d6 at 373 K) 9.69 (s, 1H), 8.52 (s, 1H), 8.21-8.20 (m, 1H), 7.66-7.63 (m, 1H), 7.40 (t, 1H), 6.90 (d, 1H), 6.83 (d, 1H), 4.41-4.39 (m, 2H), 4.20-4.10 (m, 1H), 4.05-4.00 (m, 2H), 3.97 (s, 3H), 3.73 (dd, 1H), 3.61-3.58 (m, 1H), 3.51-3.47 (m, 1H), 3.42 (dd, 1H), 2.26-2.14 (br m, 1H), 2.00-1.87 (br m, 1H); Mass spectrum MH+ 461.

Sources & evidence

ORD record: ord-3b165d4db5cf4c8a8dbd691fc589aaa1
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659279B2

Reaction notes

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