Isopropylamine → HCID 59645231, compound

HRID 2252812Notes

Reaction equation

HRID 2252812 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:11]=1[C:12]([O:14]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21]([NH2:24])([CH3:23])[CH3:22]>>[F:20][C:17]1[CH:18]=[CH:19][C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[C:11]([C:12]([NH:24][CH:21]([CH3:23])[CH3:22])=[O:14])[CH:16]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 11984297HCID 11984297, compound

Product 1

HCID 59645231HCID 59645231, compound

Conditions

Temperature
70 °C

Procedure

In an oven-dried high pressure bomb reactor apparatus was placed dry toluene (30 mL) and nitrogen was bubbled through the solution. Methyl 2-{[(tert-butoxycarbonyl)amino]methyl}-5-fluorobenzoate (4.0 g, 14.1 mmol, prepared as described in Example 3C, Step 4) and isopropylamine (12.0 mL, 0.14 mol) were added to the vessel. The bomb was sealed and heated to 70° C. overnight. The vessel was cooled and the reaction was concentrated to dryness in vacuo. The residue was purifed by flash column chromatography (ISCO column, 120 g silica) running a 0-30% acetone/hexane gradient over 30 minutes. The product fractions were concentrated to give the title compound as a white solid.

Workup

  1. customIn an oven-dried high pressure bomb reactor apparatus was placed dry
  2. customtoluene (30 mL) and nitrogen was bubbled through the solution
  3. customThe bomb was sealed
  4. temperatureThe vessel was cooled
  5. concentrationthe reaction was concentrated to dryness in vacuo
  6. customover 30 minutes
  7. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-b0ea0cc5a8cc44b594f18606f6ab3d3b
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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