Benzylamine → HCID 131728449, compound

HRID 1927467Notes

Reaction equation

HRID 1927467 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]([C:13]1[CH:14]=[C:15]([CH3:39])[C:16]2[O:22][C:21]3[C:23]([Cl:35])=[CH:24][C:25]([N:27]([C:31](=[O:34])[CH2:32]Cl)[CH2:28][CH2:29]Cl)=[CH:26][C:20]=3[CH2:19][S:18](=[O:37])(=[O:36])[C:17]=2[CH:38]=1)=[O:12]>CN(C=O)C>[CH3:9][O:10][C:11]([C:13]1[CH:14]=[C:15]([CH3:39])[C:16]2[O:22][C:21]3[C:23]([Cl:35])=[CH:24][C:25]([N:27]4[CH2:28][CH2:29][N:8]([CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH2:32][C:31]4=[O:34])=[CH:26][C:20]=3[CH2:19][S:18](=[O:36])(=[O:37])[C:17]=2[CH:38]=1)=[O:12]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 131728447HCID 131728447, compound

Product 1

HCID 131728449HCID 131728449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Benzylamine (0.17 mL, 1.581 mmol) was added to a solution of Example 57k (0.4 g, 0.79 mmol) in DMF (5 mL) and stirred at 80° C. for 5 h. The reaction mixture was concentrated, treated with water and extracted with chloroform. The organic layer was washed with water, brine, dried and concentrated to obtain the crude title compound which was purified using flash chromatography (silica gel, 1% methanol/chloroform). Yield: 125 g, (29.2%); 1H NMR (DMSO-d6,): δ 2.68 (s, 3H, CH3), 2.8 (t, 2H, CH2), 3.2 (s, 2H, CH2), 3.63 (s, 2H, CH2), 3.7 (t, 2H, CH2), 3.88 (s, 3H, OCH3), 5.31 (s, 2H, CH2), 7.29-7.38 (m, 5H, Ar), 7.66 (s, 1H, Ar), 7.73 (s, 1H, Ar), 8.16 (s, 1H, Ar), 8.19 (s, 1H, Ar); MS: m/e (ES+) 541 (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. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03196460bd274eeeb056ef67dd0e0e9d
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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