Furfurylamine → HCID 17199903, compound

HRID 1945420Notes

Reaction equation

HRID 1945420 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)=[O:7].[CH2:23]([NH2:29])[C:24]1[O:28][CH:27]=[CH:26][CH:25]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C)C1C=CN=CC=1.CN(C=O)C>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:29][CH2:23][C:24]1[O:28][CH:27]=[CH:26][CH:25]=1)=[O:14])=[O:7]

Participants

6

Reactant 3

HCID 3438FurfurylamineHCID 668139HCID 668139, compoundHCID 2724699PyBOP

Product 1

HCID 17199903HCID 17199903, compoundYield 115%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To solution of 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid (100.3 mg, 0.3 mmol), furfuryl amine (58.3 mg, 0.06 ml, 0.6 mmol), 4-dimethylaminopyridine (73.4 mg, 0.6 mmol) and PyBOP (312.3 mg, 1.0-mmol) in DMF 5.0 mL was stirred. Reaction mixture was separated by EtoAC and brine. The organic phase was dried (MgSO4 anh) and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=10:1) to give 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-furan-2-ylmethyl-benzamide as a white solid (144.6 mg, 90% yield).

Workup

  1. customReaction mixture
  2. customwas separated by EtoAC and brine
  3. dry with materialThe organic phase was dried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=10:1)

Sources & evidence

ORD record
ord-dfdcca4816de4b088acf007d559569de
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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