1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 56592711, compound

HRID 2359275Notes

Reaction equation

HRID 2359275 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][S:11]([NH2:14])(=[O:13])=[O:12].[Cl:15][C:16]1[C:17]([S:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)=[CH:18][C:19]([F:25])=[C:20]([CH:24]=1)[C:21](O)=[O:22].CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:15][C:16]1[C:17]([S:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)=[CH:18][C:19]([F:25])=[C:20]([CH:24]=1)[C:21]([NH:14][S:11]([CH3:10])(=[O:13])=[O:12])=[O:22]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 58046335HCID 58046335, compound

Product 1

HCID 56592711HCID 56592711, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (0.248 mL, 1.422 mmol) and methansulfonamide (135 mg, 1.42 mmol) were added to a mixture of 5-chloro-4-(3,4-dichlorophenylthio)-2-fluorobenzoic acid (Preparation 159, 250 mg, 0.71 mmol), 4-dimethylaminopyridine (130 mg, 1.07 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (204 mg, 1.07 mmol) in DCM (4.4 mL) and the reaction stirred at room temperature for 18 hours. The reaction was concentrated to dryness and the residue taken up in EtOAc (30 mL), washed with 1N aq. HCl (2×5 mL), brine (4×5 mL), dried over MgSO4, filtered and evaporated to give a yellow solid. The solid was purified using silica gel column chromatography eluting with 19:1 DCM:heptanes to afford the title compound as a white solid (221 mg, 73%).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. washwashed with 1N aq. HCl (2×5 mL), brine (4×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a yellow solid
  7. customThe solid was purified
  8. washeluting with 19:1 DCM

Sources & evidence

ORD record
ord-335121ce6baf472a96ad5d9c9ef80a63
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

Loading…