HCID 58923859, compound → HCID 136353471, compound

HRID 1364075Notes

Reaction equation

HRID 1364075 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]3[N:22]4[CH2:23][CH2:24][CH2:25][N:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:27][C:21]4=[N:20][C:14]=3[C:15]([NH2:19])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[NH2:19][C:15]1[C:14]2[N:20]=[C:21]3[CH2:27][N:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:25][CH2:24][CH2:23][N:22]3[C:13]=2[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[N:16]=1

Participants

4

Reactant 1

HCID 58923859HCID 58923859, compound

Product 1

HCID 136353471HCID 136353471, compoundYield 22.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(Benzyloxy)-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine, (6.37 g, 14.56 mmol) prepared as described in Example 369, was dissolved in methanol (150 mL) and transferred to a hydrogenation vessel charged with 10% palladium on carbon (12.4 g, 116 mmol). The vessel was purged with nitrogen gas and placed under hydrogen pressure (50 psi, 3.45×105 Pa) and shaken for 3 days at ambient temperature. The catalyst was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue crystallized from isopropanol. The material was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 47-minute gradient from 5:95 to 50:50) and crystallized from isopropanol to provide 1.15 g of 6-amino-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-3-ol.

Workup

  1. customtransferred to a hydrogenation vessel
  2. customThe vessel was purged with nitrogen gas
  3. customThe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue crystallized from isopropanol
  6. customThe material was purified by column chromatography on silica gel (
  7. washeluting with 2 N ammonia in methanol/chloroform in a 47-minute gradient from 5:95 to 50:50) and
  8. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-cb2fe635acf54f0cb519792cd0ecbd6f
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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