2-(Methylamino)ethanol → HCID 16117216, compound

HRID 1162225Notes

Reaction equation

HRID 1162225 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[O:28][CH2:29][C:30](OC)=[O:31])[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[CH3:34][NH:35][CH2:36][CH2:37][OH:38]>>[OH:38][CH2:37][CH2:36][N:35]([CH3:34])[C:30](=[O:31])[CH2:29][O:28][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[C:18]([NH:17][C:13]1[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[N:9]=[CH:10]3)=[N:19][CH:20]=[N:21]2

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 86627835HCID 86627835, compound

Product 1

HCID 16117216HCID 16117216, compoundYield 59.7%

Procedure

Using the same procedure as in Example 5, methyl [(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]acetate (200 mg, 0.45 mmol) was reacted with 2-(methylamino)ethanol (0.219 ml, 2.73 mmol) to give the title compound as a white solid (130 mg, 59%), except that the reaction was run at 45° C. for 18 hours. NMR Spectrum (2 rotamers, ratio 2/1) 2.97 and 3.08 (s, 3H), 3.62-3.43 (m, 4H), 4.73 and 4.99 (t, 1H), 5.16 and 5.23 (s, 2H), 5.77 (s, 2H), 6.96 (d, 1H), 7.37-7.18 (m, 3H), 7.75-7.69 (m, 3H), 7.90 (m, 1H), 8.15 (s, 1H), 8.53 (m, 2H), 8.57 (s, 1H), 11.20 and 11.21 (br s, 1H); Mass spectrum MH+ 484.

Sources & evidence

ORD record
ord-b87a311882aa429998294759f212756c
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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