Triethylamine → HCID 11381222, compound

HRID 2224661Notes

Reaction equation

HRID 2224661 reaction equation
[C:1]1(=[O:24])[N:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10](Cl)[C:11](=[O:17])[NH:12]3)[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12.C(N(CC)CC)C>[Pd].CN(C)C=O>[C:4]1(=[O:19])[N:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][C:11](=[O:17])[NH:12]3)[C:1](=[O:24])[C:2]2=[CH:23][CH:22]=[CH:21][CH:20]=[C:3]12

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 11382248HCID 11382248, compound

Product 1

HCID 11381222HCID 11381222, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

A 10 L pressure reactor was charged with dry Pd/C (30 gm), 4-(2′-phthalimidoethyl)-3-chloro-1,3-dihydro-2H-indol-2-one (300 gm, 0.882 mol), triethylamine (133 gm, 0.952 mol) and dimethylformamide (6 L). The reaction mixture was hydrogenated at 30-50° C. and 70-75 psi for 2 hours. The catalyst was filtered at 50° C. and filtrate was concentrated in vacuum. Water (1.5 L) was added to residue and slurry was stirred for 30 minutes at 30° C. The solids were filtered at suction and washed with water, and dried in oven at 60-70° C. to give title compound as yellow solid (225 gm, 83.3%).

Workup

  1. customwas hydrogenated at 30-50° C.
  2. filtrationThe catalyst was filtered at 50° C.
  3. concentrationfiltrate was concentrated in vacuum
  4. additionWater (1.5 L) was added to residue and slurry
  5. filtrationThe solids were filtered at suction
  6. washwashed with water
  7. customdried in oven at 60-70° C.

Sources & evidence

ORD record
ord-795dbe105e35472cae8d48c64f7e81f4
Source dataset
uspto-grants-2008_05
Patent number
US07378439B2

Reaction notes

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