Glycolic Acid → HCID 11431121, compound

HRID 1442984Notes

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][C@H:22]3[CH2:26][CH2:25][CH2:24][NH: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][C@H:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:30](=[O:31])[CH2:29][OH:32])[N:13]=[CH:12][N:11]=1

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 68676941HCID 68676941, compound

Product 1

HCID 11431121HCID 11431121, compoundYield 47%

Procedure

The procedure described in Example 1 was repeated using N-(3-chloro-4-fluorophenyl)-7-methoxy-5-[(2R)-pyrrolidin-2-ylmethoxy]-quinazolin-4-amine (90 mg) and glycolic acid (19 mg) to give the title compound in 47% yield; NMR Spectrum (DMSO-d6) 9.90 (s, 1H), 8.42 (s, 1H), 8.15 (dd, 1H), 7.70-7.60 (m, 1H), 7.40 (t, 1H), 6.90 (d, 1H), 6.78 (d, 1H), 4.65-4.53 (m, 2H), 4.42-4.37 (m, 1M), 4.20-4.11 (m, 1H), 4.03 (d, 1H), 3.90 (s, 3H), 3.45-3.35 (m, 3H), 2.10-1.82 (m, 41); Mass spectrum MH+ 461.

Sources & evidence

ORD record: ord-2c9807fbfcd641edb5f1105af73a4547
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659279B2

Reaction notes

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