Triethylamine → HCID 45258643, compound

HRID 878469Notes

Reaction equation

HRID 878469 reaction equation
Cl[C:2](=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][C:18]=1[NH2:29])([O-:16])=[O:15].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][C:18]=1[NH:29][C:2](=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4586585Methyl 8-chloro-8-oxooctanoateHCID 125954834-Nitro[1,1'-biphenyl]-3-amine

Product 1

HCID 45258643HCID 45258643, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 8-chloro-8-oxooctanoate (200 mg, 0.97 mmol) in DMF at 0° C. was added a solution of 4-nitrobiphenyl-3-amine (207 mg, 0.97 mmol) and triethylamine (0.46 mL, 3.3 mmol) in DMF 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 and purified by biotage column chromatography to give methyl 8-(4-nitrobiphenyl-3-ylamino)-8-oxooctanoate (279 mg)

Workup

  1. washwashed with 1 N HCl, saturated sodium bicarbonate solution and brine
  2. concentrationThe separated organic layer was concentrated
  3. custompurified by biotage column chromatography

Sources & evidence

ORD record
ord-3c4cfdb62f7e4d8890520774c023d996
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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