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

HRID 1162269Notes

Reaction equation

HRID 1162269 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](OC)=[O:29])[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[CH2:36]([CH2:38][NH2:39])[OH: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:39][CH2:38][CH2:36][OH:37])=[O:29])[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 86627837methyl (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate

Product 1

HCID 16118037(2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]-N-(2-hydroxyethyl)propanamideYield 80.9%

Procedure

Using the same procedure as in Example 26, methyl (2R)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (200 mg, 0.42 mmol) was reacted with ethanolamine (0.15 mL, 2.5 mmol) to give the title compound as a white solid (170 mg, 80%); NMR Spectrum 1.65 (d, 3H), 3.22 (q, 2H), 3.41-3.45 (m, 2H), 4.75 (t, 1H), 5.22 (q, 1H), 5.70 (s, 2H), 7.01-7.12 (m, 4H), 7.36 (dd, 2H), 7.72-7.76 (m, 3H), 8.17 (s, 1H), 8.47 (m, 1H), 8.53 (s, 1H), 8.56 (s, 1H), 10.73 (br s, 1H); Mass spectrum MH+ 501.

Sources & evidence

ORD record
ord-24ab2ab6a2fd4f159a8b31a2d3cca6b0
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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