HCID 18470638, compound → HCID 18470651, compound

HRID 2228493Notes

Reaction equation

HRID 2228493 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[C:9]([O:12]CC3C=CC=CC=3)[CH:10]=2)[N:5]=[C:4]([N:22]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:30])[CH2:24][CH2:23]2)[CH:3]=1>[Pd].C(O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([N:22]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[O:30])[CH2:24][CH2:23]2)[CH:3]=1

Participants

4

Reactant 1

HCID 18470638HCID 18470638, compound

Product 1

HCID 18470651HCID 18470651, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on charcoal (250 mg) was added to a solution of 4-amino-6-benzyloxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinoline (1.01 g, 0.002 mol) in ethanol (100 ml) and the reaction stirred at room temperature under a hydrogen atmosphere of 414 kPa (60 p.s.i.) for 72 hours. The reaction mixture was filtered through Arbocel™, washing well with further ethanol. The filtrate was evaporated under reduced pressure to give the subtitle compound as a solid (770 mg, 93%). Rf 0.40 (0.880 aqueous ammonia:methanol:dichloromethane 2:14:84, v/v). MS m/z 402 (MH)+.

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel™
  2. washwashing well with further ethanol
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-422c098763544b17bafefc09a997d1e8
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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