1-[(6-fluoropyridin-3-yl)methyl]-1H-indazol-5-amine → (2R)-2-{[4-({1-[(6-fluoropyridin-3-yl)methyl]-1H-indazol-5-yl}amino)quinazolin-5-yl]oxy}-N,N-dimethylpropanamide

HRID 1162232Notes

Reaction equation

HRID 1162232 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].[F:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([NH2:37])=[CH:34][CH:35]=3)[CH:30]=[N:29]2)=[CH:23][CH:22]=1>>[F:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([NH:37][C:9]4[C:8]5[C:13](=[CH:14][CH:15]=[CH:16][C:7]=5[O:6][C@H:4]([CH3:5])[C:3]([N:2]([CH3:19])[CH3:1])=[O:18])[N:12]=[CH:11][N:10]=4)=[CH:34][CH:35]=3)[CH:30]=[N:29]2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 686183641-[(6-fluoropyridin-3-yl)methyl]-1H-indazol-5-amineHCID 136346624(2R)-N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide

Product 1

HCID 16117351(2R)-2-{[4-({1-[(6-fluoropyridin-3-yl)methyl]-1H-indazol-5-yl}amino)quinazolin-5-yl]oxy}-N,N-dimethylpropanamideYield 60.2%

Procedure

Using the same procedure as in Example 18, (2R)—N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide (200 mg, 0.77 mmol) and 1-[(6-fluoropyridin-3-yl)methyl]-1H-indazol-5-amine (204 mg, 0.84 mmol) were reacted to give the title compound as a white solid (225 mg, 60%); NMR Spectrum (CDCl3) 1.73 (d, 3H), 3.07 (s, 3H), 3.15 (s, 3H), 5.44 (q, 1H), 5.59 (s, 2H), 6.84 (m, 2H), 7.37 (d, 1H), 7.8-7.45 (m, 3H), 7.87 (dd, 1H), 8.07 (s, 1H), 8.21 (s, 1H), 8.44 (s, 1H), 8.62 (s, 1H); Mass spectrum 486.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1eb9d770ee2a4a318962962863434afb
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

Loading…