1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86686553, compound

HRID 1528060Notes

Reaction equation

HRID 1528060 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16]2)[CH:12]=[CH:11][C:10]=1[N:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25](=[O:30])[C:24]([C:31](O)=[O:32])=[N:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:35][NH:36][O:37][CH3:38].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(N(CC)CC)C.C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19]2)[CH:12]=[CH:11][C:10]=1[N:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25](=[O:30])[C:24]([C:31]([N:36]([O:37][CH3:38])[CH3:35])=[O:32])=[N:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 86686552HCID 86686552, compound

Product 1

HCID 86686553HCID 86686553, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 1-[2-(benzyloxy)-4-(3,4-difluoro-1H-pyrrol-1-yl)phenyl]-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylic acid (0.5 THF solvate, 4.67 g), N,O-dimethylhydroxylamine hydrochloride (1.11 g), WSC (2.19 g), HOBt (1.54 g) and triethylamine (1.59 mL) in DMF (75 mL) was stirred at room temperature for 6 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, THF), and recrystallized from hexane/THF to give the title compound (4.51 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, THF)
  6. customrecrystallized from hexane/THF

Sources & evidence

ORD record
ord-8396c8b90b26442fb6241b72906a8b6e
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

Loading…