2-[(5-amino-1H-indazol-1-yl)methyl]benzonitrile → (2R)-2-[(4-{[1-(2-cyanobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]-N,N-dimethylpropanamide

HRID 1162234Notes

Reaction equation

HRID 1162234 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].[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH2:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[C:33]#[N:34])[N:25]=[CH:24]2>>[C:33]([C:32]1[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=1[CH2:30][N:26]1[C:27]2[C:23](=[CH:22][C:21]([NH:20][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:29][CH:28]=2)[CH:24]=[N:25]1)#[N:34]

Participants

3

Reactant 2

HCID 686188172-[(5-amino-1H-indazol-1-yl)methyl]benzonitrileHCID 136346624(2R)-N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide

Product 1

HCID 16117481(2R)-2-[(4-{[1-(2-cyanobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]-N,N-dimethylpropanamideYield 81%

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 2-[(5-amino-1H-indazol-1-yl)methyl]benzonitrile (1.1 equivalents) were reacted to give the title compound as a beige foam (334 mg, 81%); NMR spectrum (CDCl3) 1.72 (d, 3H), 3.06 (s, 3H), 3.14 (s, 3H), 5.43 (q, 1H), 5.83 (s, 2H), 6.81 (d, 1H), 7.01 (d, 1H), 7.37 (t, 1H), 7.42-7.47 (m, 3H), 7.60 (t, 1H), 7.70 (d, 1H), 7.86 (d, 1H), 8.10 (s, 1H), 8.47 (s, 1H), 8.62 (s, 1H), 10.92 (br s, 1H); Mass spectrum MH+ 492.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-174ad06321c0450d86fb2d3f708c438b
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

Loading…