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

HRID 1162240Notes

Reaction equation

HRID 1162240 reaction equation
F[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:12][C:13]1[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[N:17]=[CH:16]3)=[N:5][CH:6]=[N:7]2.[C:30]([O:35][CH3:36])(=[O:34])[C@@H:31]([CH3:33])[OH:32]>>[F:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[CH2:22][N:18]1[C:19]2[C:15](=[CH:14][C:13]([NH:12][C:4]3[C:3]4[C:8](=[CH:9][CH:10]=[CH:11][C:2]=4[O:32][C@@H:31]([CH3:33])[C:30]([O:35][CH3:36])=[O:34])[N:7]=[CH:6][N:5]=3)=[CH:21][CH:20]=2)[CH:16]=[N:17]1

Participants

3

Reactant 2

HCID 637514(+)-Methyl lactateHCID 686194305-fluoro-N-[1-(3-fluorobenzyl)-1H-indazol-5-yl]quinazolin-4-amine

Product 1

HCID 86627836methyl (2S)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate

Procedure

The 5-fluoro-N-[1-(3-fluorobenzyl)-1H-indazol-5-yl]quinazolin-4-amine (2.4 g, 6.48 mmol) was reacted as in Example 5 starting material, except that (R)-methyl lactate was used instead of (s)-methyl lactate, to give methyl (2S)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate:

Sources & evidence

ORD record
ord-e8a650070c774af59495d88ee9ebe856
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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