Dimethylamine → HCID 10192651, compound

HRID 991835Notes

Reaction equation

HRID 991835 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)[N:19]2[CH2:23]CC[CH2:20]2)C2C=CC=CC=2N=N1.[C:34]([C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41](=[O:46])[CH2:40]2)(O)=[O:35].CNC.C(N(CC)CC)C>ClCCl>[CH3:20][N:19]([CH3:23])[C:34]([C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41](=[O:46])[CH2:40]2)=[O:35]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 2724699PyBOPHCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 10192651HCID 10192651, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), dimethylamine (5.6 mL of 2.0 M in THF, 11.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 3 hours, the reaction was diluted with more dichloromethane, washed with water, saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 480 mg (42%) of 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid dimethylamide.

Workup

  1. washwashed with water, saturated sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1bda824c728c4c889d9e361dc6c0952d
Source dataset
uspto-grants-2002_10
Patent number
US06465507B2

Reaction notes

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