Triethylamine → HCID 66778512, compound

HRID 878475Notes

Reaction equation

HRID 878475 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:20](=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:11][C:20](=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4586585Methyl 8-chloro-8-oxooctanoateHCID 10582926N-cyclopropylbenzene-1,2-diamine

Product 1

HCID 66778512HCID 66778512, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N1-cyclopropylbenzene-1,2-diamine (221 mg, 1.49 mmol) and triethylamine (0.3 mL, 2.2 mmol) in DMF was added a solution of methyl 8-chloro-8-oxooctanoate (260 mg, 1.3 mmol) in DMF at 0° C. drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated to give crude methyl 8-(2-(cyclopropylamino)phenylamino)-8-oxooctanoate (390 mg)

Workup

  1. washwashed with 1 N HCl, saturated sodium bicarbonate solution and brine
  2. concentrationThe separated organic layer was concentrated

Sources & evidence

ORD record
ord-03de56306c0e45c49105e5a3fd22e46e
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

Loading…