1-(3-Fluorobenzyl)-1H-indazol-5-amine → (R)-2-(4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-5-yloxy)-N,N-dimethylpropanamide

HRID 1162229Notes

Reaction equation

HRID 1162229 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[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[CH2:24][N:25]1[C:33]2[C:28](=[CH:29][C:30]([NH2:34])=[CH:31][CH:32]=2)[CH:27]=[N:26]1>>[F:20][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[CH2:24][N:25]1[C:33]2[C:28](=[CH:29][C:30]([NH:34][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:31][CH:32]=2)[CH:27]=[N:26]1

Participants

3

Reactant 2

HCID 71470731-(3-Fluorobenzyl)-1H-indazol-5-amineHCID 136346624(2R)-N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide

Product 1

HCID 16117348(R)-2-(4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-5-yloxy)-N,N-dimethylpropanamideYield 74%

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-(3-fluorobenzyl)-1H-indazol-5-amine (193 mg, 0.8 mmol) were reacted to give the title compound as a pale solid (272 mg, 74%); NMR Spectrum (CDCl3) 1.72 (d, 3H), 3.06 (s, 3H), 3.14 (s, 3H), 5.43 (q, 1H), 5.59 (s, 2H), 6.81 (d, 1H), 6.87 (d, 1H), 6.96 (m, 2H), 7.25 (m, 1H), 7.34 (d, 1H), 7.47 (d, 1H), 7.60 (t, 1H), 7.84 (dd, 1H), 8.07 (s, 1H), 8.42 (s, 1H), 8.62 (s, 1H); Mass spectrum 485.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9d0f4a925a4c4b5d9236d2e3ce291081
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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