methyl (S)-lactate → methyl (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate

HRID 1162244Notes

Reaction equation

HRID 1162244 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:24]([OH:26])=[CH:23][CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[C:30]([O:35][CH3:36])(=[O:34])[C@H:31]([CH3:33])O>>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[O:26][C@H:31]([CH3:33])[C:30]([O:35][CH3:36])=[O:34])[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

3

Reactant 2

HCID 94386methyl (S)-lactateHCID 1363467214-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-ol

Product 1

HCID 86627837methyl (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoateYield 69%

Procedure

4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-ol was reacted with (S)-methyl lactate as described in Example 5, starting material to give methyl (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (760 mg, 69%); Mass spectrum 472.

Sources & evidence

ORD record
ord-52a716b689cd4a1babbcfa6adc8496dd
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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