Ethylamine → (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]-N-ethylpropanamide

HRID 1162268Notes

Reaction equation

HRID 1162268 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=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:27]([CH3:32])[C:28]([O:30]C)=O)[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[CH2:36]([NH2:38])[CH3:37]>>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=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:27]([CH3:32])[C:28]([NH:38][CH2:36][CH3:37])=[O:30])[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

3

Reactant 2

HCID 6341EthylamineHCID 86627837methyl (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate

Product 1

HCID 16118036(2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]-N-ethylpropanamideYield 76%

Procedure

Using the same procedure as in Example 5, methyl (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (250 mg, 0.53 mmol) was reacted with ethylamine to give the title compound as a white solid (195 mg, 76%); NMR Spectrum 1.04 (t, 3H), 1.65 (d, 3H), 3.14-3.20 (m, 2H), 5.16 (q, 1H), 5.71 (s, 2H), 7.01 (d, 1H), 7.04-7.12 (m, 3H), 7.36 (dd, 2H), 7.72-7.78 (m, 3H), 8.17 (s, 1H), 8.44 (m, 1H), 8.53 (s, 1H), 8.56 (s, 1H), 10.68 (br s, 1H); Mass spectrum MH+ 485.

Sources & evidence

ORD record
ord-207e1067048342aca55c24f3f59a6ab1
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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