Pyridinium chloride → 4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-ol

HRID 1162214Notes

Reaction equation

HRID 1162214 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([NH:13][C:14]1[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[N:18]=[CH:17]3)=[N:6][CH:7]=[N:8]2.Cl.N1C=CC=CC=1>N1C=CC=CC=1>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:19]1[C:20]2[C:16](=[CH:15][C:14]([NH:13][C:5]3[C:4]4[C:3]([OH:2])=[CH:12][CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][N:6]=3)=[CH:22][CH:21]=2)[CH:17]=[N:18]1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 686187925-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine

Product 1

HCID 1363467194-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-olYield 100.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine (10.1 g, 27.4 mmol) and pyridine hydrochloride (15.8 g, 137 mmol) in pyridine (150 ml) was heated at reflux for 3 hours. After cooling and evaporation of the solvents, the residue was triturated in 5% aqueous sodium bicarbonate and the resulting mixture was stirred for 30 minutes. The yellowish precipitate was filtered, washed with water and ether, and dried over P2O5 under high vacuum to give 4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-ol as a solid (10.1 g, 100%); NMR spectrum 5.76 (s, 2H), 6.67 (m, 2H), 6.96 (d, 1H), 7.29 (m, 1H), 7.42 (m, 1H), 7.52 (dd, 1H), 7.74-7.66 (m, 2H), 8.13 (s, 1H), 8.33 (s, 2H), 8.52 (d, 1H); Mass spectrum MH+ 369.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. customevaporation of the solvents
  5. customthe residue was triturated in 5% aqueous sodium bicarbonate
  6. filtrationThe yellowish precipitate was filtered
  7. washwashed with water and ether
  8. dry with materialdried over P2O5 under high vacuum

Sources & evidence

ORD record
ord-0dc5c2fc1e21469b9b7b905462872429
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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