Isobutylamine → HCID 18324821, compound

HRID 1250905Notes

Reaction equation

HRID 1250905 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])C1=S)[CH:2]=[CH2:3].[CH2:19](N)C(C)C>O>[Cl:16][C:15]1[C:10]([NH:6][CH2:7][CH2:8][CH2:9][NH:4][CH2:1][CH:2]([CH3:3])[CH3:19])=[C:11]([CH3:17])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 9925711HCID 9925711, compound

Product 1

HCID 18324821HCID 18324821, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Under cooling the hydrobromide salt of Example 12, Step B (6.82 g) was mixed with isobutylamine (5.85 g). The mixture was warmed to 85° C. under nitrogen until homogeneous and then refluxed for 2.5 hours. After cooling, it was diluted with water and the basic solution extracted with dichloromethane. The extracts were washed with 20% aqueous sodium chloride, dried over anhydrous potassium carbonate and evaporated to a brown oil which was flash chromatographed (on Merck-60 flash silica gel). The less polar impurities were eluted with 1:1 hexane- EtOAc and the desired material with 95:5:0.1 dichloromethane-methanol-ammonium hydroxide. The low melting material (3.82 g, 75%) was used as such in the next step.

Workup

  1. temperaturethen refluxed for 2.5 hours
  2. temperatureAfter cooling
  3. extractionthe basic solution extracted with dichloromethane
  4. washThe extracts were washed with 20% aqueous sodium chloride
  5. dry with materialdried over anhydrous potassium carbonate
  6. customevaporated to a brown oil which
  7. customchromatographed (on Merck-60 flash silica gel)
  8. washThe less polar impurities were eluted with 1:1 hexane- EtOAc

Sources & evidence

ORD record
ord-a607ca673d794e0c811f97db384a2a01
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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