Ammonia → (R)-2-(4-(1-(pyridin-2-ylmethyl)-1H-indazol-5-ylamino)quinazolin-5-yloxy)propanamide

HRID 1162211Notes

Reaction equation

HRID 1162211 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[O:28][C@H:29]([CH3:34])[C:30]([O:32]C)=O)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[NH3:35]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[O:28][C@H:29]([CH3:34])[C:30]([NH2:35])=[O:32])[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86627834methyl (2R)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate

Product 1

HCID 16117085(R)-2-(4-(1-(pyridin-2-ylmethyl)-1H-indazol-5-ylamino)quinazolin-5-yloxy)propanamideYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (2R)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (250 mg, 0.55 mmol) in methanol (3 ml) was saturated with ammonia by bubbling gaseous ammonia into the solution for a few minutes. The tube containing the solution was sealed and the mixture was stirred for 48 hours at room temperature. The precipitate was filtered, washed with ether and dried to give the title compound as a white solid (165 mg, 65%); NMR Spectrum 1.66 (d, 3H), 5.14 (q, 1H), 5.77 (s, 2H), 6.94 (d, 1H), 7.02 (d, 1H), 7.30 (m, 1H), 7.36 (d, 1H), 7.55 (br s, 1H), 7.78-7.67 (m, 4H), 7.89 (br s, 1H), 8.15 (s, 1H), 8.52 (m, 3H), 10.80 (br s, 1H); Mass spectrum MH+ 440.

Workup

  1. customby bubbling gaseous ammonia into the solution for a few minutes
  2. additionThe tube containing the solution
  3. customwas sealed
  4. filtrationThe precipitate was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-a9723c9d218547e08f677ad8bd6cf27a
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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