1-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-amine → (2R)-N,N-dimethyl-2-[(4-{[1-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanamide

HRID 1162235Notes

Reaction equation

HRID 1162235 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].[O:20]1[CH:24]=[CH:23][N:22]=[C:21]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>>[CH3:1][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]([NH:35][C:31]1[CH:30]=[C:29]3[C:34](=[CH:33][CH:32]=1)[N:26]([CH2:25][C:21]1[O:20][CH:24]=[CH:23][N:22]=1)[N:27]=[CH:28]3)=[N:10][CH:11]=[N:12]2)[CH3:5]

Participants

3

Reactant 2

HCID 686189121-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-amineHCID 136346624(2R)-N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide

Product 1

HCID 16117482(2R)-N,N-dimethyl-2-[(4-{[1-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanamideYield 80%

Procedure

Using the same procedure as in Example 18, (2R)—N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide (212 mg, 0.81 mmol) and 1-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-amine (1 equivalents) were reacted to give the title compound as a beige foam (295 mg, 80%); NMR spectrum (CDCl3) 1.73 (d, 3H), 3.06 (s, 3H), 3.14 (s, 3H), 5.43 (q, 1H), 5.71 (s, 2H), 6.81 (d, 1H), 7.09 (s, 1H), 7.48-7.53 (m, 2H), 7.58-7.62 (m, 2H), 7.88 (d, 1H), 8.07 (s, 1H), 8.41 (s, 1H), 8.61 (s, 1H), 10.92 (br s, 1H); Mass spectrum MH+ 458.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9e716a937a74489f88fb2dc62150a388
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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