Water → HCID 22175281, compound

HRID 1797692Notes

Reaction equation

HRID 1797692 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[S:17][C:18]([C:22]([OH:24])=O)=[C:19]([CH3:21])[N:20]=3)[CH:14]=2)[C:9](=[O:25])[N:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:7]=1[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:2][CH2:3][CH3:4].Cl.C[N:41](C)CCCN=C=N.[NH4+].ON1C2C=CC=CC=2N=N1.O>CN(C)C=O>[C:35]([O:34][C:32](=[O:33])[NH:31][CH2:30][C:7]1[N:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:9](=[O:25])[C:10]2[C:15]([C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][C:13]([C:16]1[S:17][C:18]([C:22]([NH2:41])=[O:24])=[C:19]([CH3:21])[N:20]=1)=[CH:12][CH:11]=2)([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 21899179Dimethylaminopropyl carbodiimide hydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 22175672HCID 22175672, compound

Product 1

HCID 22175281HCID 22175281, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-butoxy-3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl)-4-methyl-1,3-thiazole-5-carboxylic acid (0.60 g, 1.1 mmol), 1-ethyl,-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.42 g, 2.2 mmol) and 1-hydroxybenzotriazole ammonium salt (0.33 g, 2.2 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 tetrahydrofuran-diisopropyl ether to give tert-butyl{6-[5-(-aminocarbonyl)-4-methyl-1,3-thiazol-2-yl]-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.58 g, 96.7%) 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 tetrahydrofuran-diisopropyl ether

Sources & evidence

ORD record
ord-2b151c1573be4469a3b5d6029d4c953e
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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