1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86702840, compound

HRID 1849495Notes

Reaction equation

HRID 1849495 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:12][S:13]([NH2:16])(=[O:15])=[O:14].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:16][S:13]([CH3:12])(=[O:15])=[O:14])=[O:8]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 86702840HCID 86702840, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5,6-dichloronicotinic acid (800 mg, 4.16 mmol), methanesulfonamide (779 mg, 8.40 mmol), EDCI (1.56 g, 8.20 mmol), and DMAP (1.00 g, 8.20 mmol) in DCM (10 mL) was stirred at room temperature for 16 h. The reaction was quenched with water (5 mL) and the resulting mixture was concentrated. The residue was adjusted to pH around 5 by 1M HCl, extracted with DCM (30 mL×3), dried over Na2SO4. The organic layer was concentrated to afford 5,6-dichloro-N-(methylsulfonyl)nicotinamide (700 mg, 62% yield). LCMS (ESI) m/z: 269.0 [M+H]+.

Workup

  1. customThe reaction was quenched with water (5 mL)
  2. concentrationthe resulting mixture was concentrated
  3. extractionextracted with DCM (30 mL×3)
  4. dry with materialdried over Na2SO4
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-fb19207a82d8486da66f01932463be20
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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