Dimethylamine → HCID 16117089, compound

HRID 1162220Notes

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]([O:32]C)=O)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[CH3:34][NH:35][CH3:36]>>[CH3:34][N:35]([CH3:36])[C:30](=[O:32])[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

Reactant 2

HCID 674Dimethylamine

HCID 86627835HCID 86627835, compound

Product 1

HCID 16117089HCID 16117089, compoundYield 73%

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 (250 mg, 0.55 mmol) was reacted with dimethylamine to give the title compound as a white solid (183 mg, 73%); NMR Spectrum 2.97 (s, 3H), 3.04 (s, 3H), 5.17 (s, 2H), 5.77 (s, 2H), 6.96 (d, 1H), 7.22 (d, 1H), 7.29 (m, 1H), 7.36 (d, 1H), 7.76-7.69 (m, 3H), 7.91 (m, 1H), 8.15 (s, 1H), 8.53 (m, 2H), 8.57 (s, 1H), 11.21 (br s, 1H); Mass spectrum MH+ 454.

Sources & evidence

ORD record: ord-6d5f42465b9e43ffacb200ab54242000
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820683B2

Reaction notes

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