1-(3-Methoxybenzyl)-1H-indazol-5-amine → (2R)-2-[(4-{[1-(3-methoxybenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]-N,N-dimethylpropanamide

HRID 1162233Notes

Reaction equation

HRID 1162233 reaction equation
[CH3:1][N:2]([CH3:19])[C:3](=[O:18])[C@H:4]([O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9](=O)[NH:10][CH:11]=[N:12]2)[CH3:5].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=1)[CH2:25][N:26]1[C:34]2[C:29](=[CH:30][C:31]([NH2:35])=[CH:32][CH:33]=2)[CH:28]=[N:27]1>>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=1)[CH2:25][N:26]1[C:34]2[C:29](=[CH:30][C:31]([NH:35][C:9]3[C:8]4[C:13](=[CH:14][CH:15]=[CH:16][C:7]=4[O:6][C@H:4]([CH3:5])[C:3]([N:2]([CH3:19])[CH3:1])=[O:18])[N:12]=[CH:11][N:10]=3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1

Participants

3

Reactant 2

HCID 534221191-(3-Methoxybenzyl)-1H-indazol-5-amineHCID 136346624(2R)-N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide

Product 1

HCID 16117352(2R)-2-[(4-{[1-(3-methoxybenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]-N,N-dimethylpropanamideYield 58%

Procedure

Using the same procedure as in Example 18, (2R)—N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide (220 mg, 0.84 mmol) and 1-(3-methoxybenzyl)-1H-indazol-5-amine (1.1 equivalents) were reacted to give the title compound as a beige foam (242 mg, 58%); NMR spectrum (CDCl3) 1.72 (d, 3H), 3.05 (s, 3H), 3.14 (s, 3H), 3.73 (s, 3H), 5.42 (q, 1H), 5.57 (s, 2H), 6.74 (s, 1H), 6.78-6.81 (m, 3H), 7.20 (t, 1H), 7.36 (d, 1H), 7.46 (d, 1H), 7.59 (t, 1H), 7.80 (d, 1H), 8.06 (s, 1H), 8.40 (s, 1H), 8.61 (s, 1H), 10.85 (br s, 1H); Mass spectrum MH+ 497.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-07e003086a4a4b739c62337ff1630cb4
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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