Isopropylamine → HCID 131728448, compound

HRID 1927466Notes

Reaction equation

HRID 1927466 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:35])[C:12]2[O:18][C:17]3[C:19]([Cl:31])=[CH:20][C:21]([N:23]([C:27](=[O:30])[CH2:28]Cl)[CH2:24][CH2:25]Cl)=[CH:22][C:16]=3[CH2:15][S:14](=[O:33])(=[O:32])[C:13]=2[CH:34]=1)=[O:8]>CN(C=O)C>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:35])[C:12]2[O:18][C:17]3[C:19]([Cl:31])=[CH:20][C:21]([N:23]4[CH2:24][CH2:25][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:28][C:27]4=[O:30])=[CH:22][C:16]=3[CH2:15][S:14](=[O:33])(=[O:32])[C:13]=2[CH:34]=1)=[O:8]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 131728447HCID 131728447, compound

Product 1

HCID 131728448HCID 131728448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Isopropylamine (2 mL, 48.72 mmol) was added to a solution of Example 57k (0.3 g, 0.59 mmol) in DMF (5 mL) and stirred at 80° C. for 3 h. The reaction mixture was concentrated, treated with water, and extracted with chloroform. The organic layer was washed with water, brine and concentrated to obtain the title compound which was purified using flash chromatography (silica gel, 2% methanol/chloroform). Yield: 0.16 g, (55.17%); 1H NMR (CDCl3,): δ 1.10 (d, 6H, 2CH3), 2.7 (s, 3H, CH3), 2.8 (q, 1H, CH), 2.86 (t, 2H, CH2), 3.41 (s, 2H, CH2), 3.7 (t, 2H, CH2), 3.92 (s, 3H, OCH3), 4.71 (s, 2H, CH2), 7.38 (d, 1H, Ar), 7.46 (d, 1H, Ar), 8.1 (s, 1H, Ar), 8.46 (s, 1H, Ar); MS: m/e (ES+) 493 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water, brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-71e4defc77fa4384869485be671250b2
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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