Methylamine → HCID 22597714, compound

HRID 1760252Notes

Reaction equation

HRID 1760252 reaction equation
CN.[Br:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([CH3:16])([CH3:15])[CH3:14])[C:7]([OH:9])=O.O[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.[CH3:27][N:28]([CH3:37])[CH2:29][CH2:30]CN=C=NCC>CN(C)C=O>[CH3:27][N:28]1[CH2:29][CH2:30][C:25]2[C:24](=[CH:23][C:22]([NH:18][C:7](=[O:9])[C:6]3[CH:10]=[CH:11][C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([Br:3])[CH:5]=3)=[CH:21][CH:26]=2)[CH2:37]1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2829923-bromo-4-tert-butylbenzoic acid

Product 1

HCID 22597714HCID 22597714, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the amine D5 (162 mg; 1.0 mmol) and 3-bromo-4-tert-butylbenzoic acid (257 mg; 1.0 mmol) in anhydrous N,N-dimethylformamide (7 ml), was treated with 1-hydroxybenzotriazole (135 mg; 1.0 mmol) and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (192 mg; 1.0 mmol) at 25° C. The mixture was shaken for 48 h before extracting the product into dichloromethane and washing with 10% aqueous NaHCO3, water and finally brine. The organic layer was dried over MgSO4 and evaporated in vacuo to afford 373 mg of the title compound in 93% yield.

Workup

  1. extractionbefore extracting the product into dichloromethane
  2. washwashing with 10% aqueous NaHCO3, water and finally brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-139103d61ca141dbb819c960c1b2fa82
Source dataset
uspto-grants-2005_01
Patent number
US06841560B2

Reaction notes

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