5-(7-methoxy-6-(3-morpholinopropoxy)-2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate → HCID 59361879, compound

HRID 1407001Notes

Reaction equation

HRID 1407001 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[N:28]([C:32]([O-:34])=[O:33])[N:27]=[CH:26]4)=[N:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=3)=[N:10]2)=[CH:5][C:4]=1[O:35][CH2:36][CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>CO.[Pd]>[NH2:19][C:15]1[CH:14]=[C:13]([C:9]2[N:8]=[C:7]([NH:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[N:28]([C:32]([O:34][C:6]([CH3:11])([CH3:7])[CH3:5])=[O:33])[N:27]=[CH:26]4)[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([O:35][CH2:36][CH2:37][CH2:38][N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH:5]=3)[N:10]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 668264595-(7-methoxy-6-(3-morpholinopropoxy)-2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 59361879HCID 59361879, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 5-(7-methoxy-6-(3-morpholinopropoxy)-2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.215 g) in MeOH (60 mL) was added Pd/C (0.21 g) and NH4CO2 (0.21 g). The mixture was heated at 60° C. for 40 mins, upon which an additional portion of NH4CO2 (0.095 g) was added, heating was continued for a further 20 minutes. The mixture was filtered to remove the Pd/C and the filtrate was concentrated under reduced pressure. The residue was taken up in CH2Cl2 (300 mL) wand was washed with water and brine. The mixture was dried (Na2SO4) and the volatiles removed in vacuo. The material was combined with an identical experiment using 0.2 g and the residue was subjected to preparative TLC (SiO2, CH2Cl2:MeOH 9:1) to give the desired product tert-butyl 5-(2-(3-aminophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate. HPLC retention time 4.67 mins.

Workup

  1. additionwas added
  2. temperatureheating
  3. filtrationThe mixture was filtered
  4. customto remove the Pd/C
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washwas washed with water and brine
  7. dry with materialThe mixture was dried (Na2SO4)
  8. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-a7e5dc656f7045df9f5887ae1c3e69a1
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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