Dichloromethane → HCID 54591946, compound

HRID 2276761Notes

Reaction equation

HRID 2276761 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[N:7][CH:8]=1.CCN(C(C)C)C(C)C.C(Cl)Cl.[C:33](=[O:37])([O:35][CH3:36])N>O>[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]([CH3:13])([CH3:12])[CH2:10][NH:9][C:6]2[N:7]=[CH:8][C:3]([CH2:2][NH:1][C:33](=[O:37])[O:35][CH3:36])=[CH:4][CH:5]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11722Methyl CarbamateHCID 81531DiisopropylethylamineHCID 67453142HCID 67453142, compound

Product 1

HCID 54591946HCID 54591946, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 20 dram vial was added 5-(aminomethyl)-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridin-2-amine (100 mg, 0.37 mmol, 1.0 equiv), DIPEA (57 mg, 0.44 mmol, 1.2 equiv) and CH2Cl2 (1.2 mL). The mixture was cooled to 0° C., and methyl carbamate (35 mg, 0.4 mmol, 1.0 equiv) was then added. The reaction was allowed to warm to rt and stirred for 2 h. The reaction mixture was then diluted with water (2 mL) and extracted with ethyl acetate (15 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography, affording 20 mg of methyl (6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridin-3-yl)methylcarbamate (m/z [M+H]=332).

Workup

  1. temperatureto warm to rt
  2. extractionextracted with ethyl acetate (15 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid that
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-33ad9095e2ef481c90b7df45b5107076
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

Loading…