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Sodium Chloride → 5,7-dihydro-6H-pyrazolo[3,4-h]quinazoline-9-carboxylic acid [6-(3-diethylamino-propoxy)-pyridin-3-yl]-amide

HRID 23436
Notes
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Reaction equation

HRID 23436 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[C:25]3[C:24](=O)[CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][N:18]=2)=[O:16])=[CH:10][CH:9]=1)[CH3:2].[CH3:29][N:30]([CH:32](N(C)C)[N:33](C)C)C.C(O)(=O)C.C(N)=N.[Na+].[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[C:25]3[C:24]4[N:33]=[CH:32][N:30]=[CH:29][C:23]=4[CH2:22][CH2:21][C:20]=3[NH:19][N:18]=2)=[O:16])=[CH:10][CH:9]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 160693Formamidine acetateHCID 102934674-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid [6-(3-diethylamino-propoxy)-pyridin-3-yl]-amide

Product 1

HCID 10287882
5,7-dihydro-6H-pyrazolo[3,4-h]quinazoline-9-carboxylic acid [6-(3-diethylamino-propoxy)-pyridin-3-yl]-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid [6-(3-diethylamino-propoxy)-pyridin-3-yl]-amide (192 mg, 0.50 mmol) and tris(dimethylamino)methane (181 mg, 1.25 mmol) is stirred in a pressure reactor at 60° C. for 5 hours. After cooling, the reaction mixture is dissolved in ethanol (5 mL), treated with formamidine acetate (1.00 g, 9.6 mmol), and stirred in a pressure reactor at 110° C. for 18 hours. The reaction mixture is poured into 10% NaCl (50 mL), treated with 1 M sodium carbonate to pH 11 and extracted with chloroform (40 mL). The extract is dried over sodium carbonate, and the solvent is evaporated under reduced pressure. The residue is triturated with diethyl ether to give pure crystalline 5,7-dihydro-6H-pyrazolo[3,4-h]quinazoline-9-carboxylic acid [6-(3-diethylamino-propoxy)-pyridin-3-yl]-amide. 1H NMR (CD3OD) t, J=7.1 Hz, 6H), 1.98 (m, 2H), 2.61 (q, J=7.1 Hz, 4H), 2.69 (m, 2H), 3.10 (m, 2H), 3.16 (m, 2H), 4.32 (t, J=6.2 Hz, 2H), 6.84 (dd, J=8.8 and 0.5 Hz, 1H), 8.17 (dd, J=8.9 and 2.7 Hz, 1H), 8.51 (dd, J=2.7 and 0.5 Hz, 1H), 8.65 (s, 1H), 9.09 (s, 1H) MW 421.507; MS (M+H)+ 422.

Workup

  1. temperatureAfter cooling
  2. stirringstirred in a pressure reactor at 110° C. for 18 hours
  3. extractionextracted with chloroform (40 mL)
  4. dry with materialThe extract is dried over sodium carbonate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-dbf56c7edf0848a7b67cd8132edc22b4
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852730B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes