Dimethylformamide → HCID 178513757, compound

HRID 455004Notes

Reaction equation

HRID 455004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[NH:10][C:11]2[S:19][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:13]=3[C:12]=2[C:20]([NH2:22])=[O:21])=[CH:4][CH:3]=1.[CH:24]1[CH:25]=[CH:26][C:27]2[N:32](O)[N:31]=[N:30][C:28]=2[CH:29]=1.CCN=C=NCCCN(C)C.Cl.CN([CH:49]=[O:50])C>>[NH:30]1[C:28]2[CH:29]=[CH:24][C:25]([C:49]([N:16]3[CH2:17][CH2:18][C:13]4[C:12]([C:20]([NH2:22])=[O:21])=[C:11]([NH:10][C:9]([NH:8][C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)=[O:23])[S:19][C:14]=4[CH2:15]3)=[O:50])=[CH:26][C:27]=2[N:32]=[N:31]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66661889HCID 66661889, compound

Product 1

HCID 178513757HCID 178513757, compoundYield 28%

Procedure

Starting material 5 (847 mg, 2.4 mmol) was suspended in DMF (8 ml) and 1H-1,2,3-benzothiazole-5-carboxylic acid (473 mg, 2.9 mmol), dry HOBt (427 mg, 2.9 mmol) and EDCl (606 mg, 2.9 mmol) were added. The brown suspension was stirred at ambient temperature over the weekend. As the reaction was not complete yet, the reaction was further stirred at 80° for 4 h. Thereby a brown solution was formed. The solvent was evaporated in vacuo and the crude product was further purified by prep. HPLC (Method 1). The product fractions were merged, the solvent was evaporated and the product lyophilized. Thereby 310 mg of the desired product 6 (0.635 mmol, 28%) were isolated as a light brown solid and additional 58 mg of the same product with 76% content which could have been purified further.

Workup

  1. stirringthe reaction was further stirred at 80° for 4 h
  2. customThereby a brown solution was formed
  3. customThe solvent was evaporated in vacuo
  4. customthe crude product was further purified by prep
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2d8be125205844ef9a346c899d29eefd
Source dataset
uspto-grants-2013_07
Patent number
US08497283B2

Reaction notes

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