Water → HCID 22175991, compound

HRID 1797629Notes

Reaction equation

HRID 1797629 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:12](=[O:32])C2C([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=CC(/C=C/C(O)=O)=CC=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=[N:42][CH2:43][CH2:44][CH2:45]N(C)C)C.[NH4+].ON1[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2N=N1.[OH2:60]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:12](=[O:32])[C:54]2[C:55]([C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)=[CH:56][C:57](/[CH:45]=[CH:44]/[C:43]([NH2:42])=[O:60])=[CH:58][CH:59]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 22175617HCID 22175617, compound

Product 1

HCID 22175991HCID 22175991, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (E)-3-[3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-4-(4-methylphenyl)-1-oxo-1,2-dihydro-6-isoquinolinyl]-2-propenic acid (0.25 g, 0.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.19 g, 1 mmol) and 1-hydroxybenzotriazole ammonium salt (0.15 g, 1 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give (E)-3-[3-[[(tert-butoxycarbonyl)-amino]methyl]-2-isobutyl-4-(4-methylphenyl)-1-oxo-1,2-dihydro-6-isoquinolinyl]-2-propenamide (0.21 g, 84.0%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-52ec2dc8aaac4168abba4bd8c32117ee
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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