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

HRID 1162231Notes

Reaction equation

HRID 1162231 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][C:21]1[S:22][C:23]([CH2:26][N:27]2[C:35]3[C:30](=[CH:31][C:32]([NH2:36])=[CH:33][CH:34]=3)[CH:29]=[N:28]2)=[CH:24][N:25]=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:36][C:32]1[CH:31]=[C:30]3[C:35](=[CH:34][CH:33]=1)[N:27]([CH2:26][C:23]1[S:22][C:21]([CH3:20])=[N:25][CH:24]=1)[N:28]=[CH:29]3)=[N:10][CH:11]=[N:12]2)[CH3:5]

Participants

3

Reactant 2

HCID 686192981-[(2-methyl-1,3-thiazol-5-yl)methyl]-1H-indazol-5-amineHCID 136346624(2R)-N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide

Product 1

HCID 16117350(2R)-N,N-dimethyl-2-{[4-({1-[(2-methyl-1,3-thiazol-5-yl)methyl]-1H-indazol-5-yl}amino)quinazolin-5-yl]oxy}propanamideYield 61.5%

Procedure

Using the same procedure as in Example 18, (2R)—N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide (261 mg, 1 mmol) and 1-[(2-methyl-1,3-thiazol-5-yl)methyl]-1H-indazol-5-amine (269 mg, 1.1 mmol) were reacted to give the title compound as a white solid (300 mg, 61%); NMR Spectrum (CDCl3) 1.73 (d, 3H), 2.62 (s, 3H), 3.07 (s, 3H), 3.15 (s, 3H), 5.43 (q, 1H), 5.71 (s, 2H), 6.82 (d, 1H), 7.43 (d, 1H), 7.49 (d, 1H), 7.61 (m, 2H), 7.86 (dd, 1H), 8.05 (s, 1H), 8.42 (s, 1H), 8.62 (s, 1H); Mass spectrum 488.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-07fbc0180d9747c3865aef043536f1ab
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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