Glycolic Acid → (3R,5S)-5-[({4-[3-Chloro-4-fluoroanilino]-7-methoxyquinazolin-5-yl}oxy)methyl]1-glycoloylpyrrolidin-3-ol

HRID 1443008Notes

Reaction equation

HRID 1443008 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:24][CH3:25])=[CH:13][C:14]=2[O:16][CH2:17][C@H:18]2[NH:22][CH2:21][C@H:20]([OH:23])[CH2:19]2)[N:9]=[CH:8][N:7]=1.[C:30](O)(=[O:33])[CH2:31][OH:32]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:24][CH3:25])=[CH:13][C:14]=2[O:16][CH2:17][C@H:18]2[N:22]([C:31](=[O:32])[CH2:30][OH:33])[CH2:21][C@H:20]([OH:23])[CH2:19]2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 68675709(3R,5S)-5-[({4-[3-chloro-4-fluoroanilino]-7-methoxyquinazolin-5-yl}oxy)methyl]pyrrolidin-3-ol

Product 1

HCID 58710728(3R,5S)-5-[({4-[3-Chloro-4-fluoroanilino]-7-methoxyquinazolin-5-yl}oxy)methyl]1-glycoloylpyrrolidin-3-olYield 53%

Procedure

The procedure described in Example 20 was repeated using (3R,5S)-5-[({4-[3-chloro-4-fluoroanilino]-7-methoxyquinazolin-5-yl}oxy)methyl]pyrrolidin-3-ol (209 mg) with glycolic acid (42 mg) to give the title compound as a white solid in 53% yield; NMR spectrum (DMSO-d6) 10.17 (s, 1H), 8.53 (s, 1H), 8.14 (dd, 1H), 7.74-7.69 (m, 1H), 7.47 (t, 1H), 6.92 (d, 1H), 6.83 (d, 1H), 5.14-5.10 (m, 1H), 4.71-4.67 (m, 1H), 4.50-4.44 (m, 1H), 4.40-4.38 (m, 1H), 4.28-4.23 (m, 1H), 4.06-4.03 (m, 2H), 3.95 (s, 3H), 3.53-3.48 (m, 3H), 2.05-2.02 (m, 2H); Mass spectrum MH+ 477.

Sources & evidence

ORD record
ord-a00ed94268b448db8b68729c4ac9b758
Source dataset
uspto-grants-2010_02
Patent number
US07659279B2

Reaction notes

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