Acetic Acid → N-(2,6-diethylphenyl)-8-({2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 81967Notes

Reaction equation

HRID 81967 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][C:24]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][C:29]=4[O:36][CH3:37])=[N:25][C:26]=3[C:17]=2[N:16]([CH3:38])[N:15]=1)=[O:13])[CH3:2].[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][C:24]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([CH2:34][N:43]5[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]5)=[CH:30][C:29]=4[O:36][CH3:37])=[N:25][C:26]=3[C:17]=2[N:16]([CH3:38])[N:15]=1)=[O:13])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86653100HCID 86653100, compound

Product 1

HCID 44556281N-(2,6-diethylphenyl)-8-({2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,6-diethylphenyl)-8-[(4-formyl-2-methoxyphenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (50 mg, 0.097 mmol) and N-methyl-piperazine (49 mg, 0.49 mmol) in 1 ml of dry DCM, NaBH(AcO)3 (123 mg, 0.58 mmol) and AcOH (25 μl) were added. The mixture was stirred at room temperature for 3 h, washed with aqueous NaHCO3, dried over Na2SO4 and evaporated to dryness. The crude was purified by flash column chromatography (DCM/MeOH 9:1) affording the title compound in 75% yield.

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude was purified by flash column chromatography (DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-9d1aee7e24c44514bd7bd08c9543713c
Source dataset
uspto-grants-2014_09
Patent number
US08846701B2

Reaction notes

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