Dimethylformamide → HCID 86592080, compound

HRID 1797706Notes

Reaction equation

HRID 1797706 reaction equation
[CH2:1]([O:5][C:6]1C2C(=CC=C(C(O)=O)C=2)[C:9](=[O:19])[N:8]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]=1[CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:2][CH2:3][CH3:4].Cl.CN[O:36][CH3:37].Cl.C(N=C=NCCCN(C)C)C.ON1[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2N=N1.C(N(CC)CC)C.[CH3:67][N:68](C)[CH:69]=[O:70]>O>[C:29]([O:28][C:26](=[O:27])[NH:25][CH2:24][C:7]1[N:8]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:9](=[O:19])[C:54]2[C:55]([C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:56][C:57]([C:69]([N:68]([O:36][CH3:37])[CH3:67])=[O:70])=[CH:58][CH:59]=2)([CH3:30])([CH3:31])[CH3:32]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22176086HCID 22176086, compound

Product 1

HCID 86592080HCID 86592080, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-butoxy-3{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinecarboxylic acid (4.46 g, 10 mmol), N,O-dimethylhydroxyamine hydrochloride (1.17 g, 12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 12 mmol), 1-hydroxybenzotriazole (1.84 g, 12 mmol) and triethylamine (1.7 ml, 12 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 resulting crystals were recrystallized from ethyl acetate-diisopropyl ether to give tert-butyl(4butoxy-2-isobutyl-6-{[methoxy(methyl)amino]carbonyl}-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (4.15 g, 84.9%) 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 resulting crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-f30d5ee3f9df4f7187af590400386256
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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