Dimethylformamide → HCID 58443022, compound

HRID 383773Notes

Reaction equation

HRID 383773 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.CN(C)[CH2:14][CH2:15][CH2:16][N:17]=[C:18]=NCC.O[N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=CC=2N=N1.[CH3:33]N(C=O)C>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:24]2[CH2:31][CH2:30][CH:29]([C:33]3[CH:18]=[N:17][CH:16]=[CH:15][CH:14]=3)[CH2:28]2)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 120854-Iodobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58443022HCID 58443022, compound

Procedure

i-5d (3.59 g, 24.2 mmol) was added to a stirred solution of 4-iodobenzoic acid (6.00 g, 24.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (5.10 g, 26.6 mmol) and 1-hydroxybenzotriazole (3.70 g, 24.2 mmol) in DMF (100 mL). After 12 h, the reaction mixture was quenched with said, aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound i-21a. m/z (ES) 379 (MH)+.

Workup

  1. customthe reaction mixture was quenched
  2. extractionaq. NaHCO3 and extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba056adf2711466b91b1d325040f1750
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

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