Dimethylformamide → HCID 178507511, compound

HRID 2369821Notes

Reaction equation

HRID 2369821 reaction equation
Cl.C[N:3](C)[CH2:4][CH2:5][CH2:6][N:7]=C=NCC.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:29]N2C(C(O)=O)=CC=N2)=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CN([CH:51]=[O:52])C>>[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:51]([C:4]1[NH:3][N:7]=[C:6](/[CH:29]=[CH:28]/[C:25]2[CH:24]=[CH:23][C:22]([OH:21])=[CH:27][CH:26]=2)[CH:5]=1)=[O:52]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131731355HCID 131731355, compound

Product 1

HCID 178507511HCID 178507511, compoundYield 10%

Procedure

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 0.377 g, 1.97 mmol) was added to a solution of 1,2-diaminobenzene (0.141 g, 1.31 mmol), 5-[2[(4-hydroxyphenyl)-vinyl]-2H-pyrazol-3-carboxylic acid (0.301 g, 1.31 mmol) and HOBt (0.266 g, 1.97 mmol) in anhydrous DMF (7 mL). The reaction was stirred under nitrogen at room temperature. After twelve hours the reaction was concentrated in vacuo and precipitated from methanol with a small amount of water. The solid was collected by vacuum filtration and further purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the corresponding amide (44 mg, 10% yield).

Workup

  1. concentrationAfter twelve hours the reaction was concentrated in vacuo
  2. customprecipitated from methanol with a small amount of water
  3. filtrationThe solid was collected by vacuum filtration
  4. customfurther purified on reverse phase

Sources & evidence

ORD record
ord-34bae3567f114d8b9311d3dbd8b8f704
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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