HCID 86747428, compound → HCID 22849506, compound

HRID 1648301Notes

Reaction equation

HRID 1648301 reaction equation
C(OC([NH:8][C@H:9]([C:17]([NH:19][CH:20]1[CH2:29][C:28]2[C:23]3=[C:24]([NH:30][C:31](=[O:32])[N:22]3[CH2:21]1)[CH:25]=[CH:26][CH:27]=2)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(C)(C)C>Cl>[O:32]=[C:31]1[N:22]2[C:23]3[C:28]([CH2:29][CH:20]([NH:19][C:17](=[O:18])[C@H:9]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH2:8])[CH2:21]2)=[CH:27][CH:26]=[CH:25][C:24]=3[NH:30]1

Participants

3

Reactant 1

HCID 86747428HCID 86747428, compound

Product 1

HCID 22849506HCID 22849506, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(-) t-Butoxycarbonyl N-(1,2,5,6-tetrahydro-2-oxo-4H-imidazo(4,5,1 -ij)quinolin-5-yl)-L-phenylalaninamide (1.8 g) was stirred in ethanolic hydrogen chloride (50 mL of 4.0 N) for 1 hour. The solvent was removed and the residual oil was partitioned between chloroform and sodium hydroxide solution. Evaporation of the chloroform gave 1.4 g of (-) N-(1,2,5,6-tetrahydro-2-oxo-4H-imidazo (4,5,1-ij)quinolin-5-yl)phenylalaninamide. This was dissolved in acetonitrile:THF (30 mL of 1:1) and phenyl isothiocyanate (675 mg, 5 mmol) was added. After 1 hour, the solvents were removed and the residual oil was chromatographed on silica gel using chloroform as the initial eluant. Elution of the column with 5% methanol:chloroform gave 1.8 g of (-) N-((phenylamino)thiocarbonyl)-N-(1,2,5,6-tetrahydro-2-oxo-4H-imidazo(4,5,1 -ij)quinolin-5-yl) phenylalamamide. This was dissolved in trifluoracetic acid (25 mL). After 1 hour the solvent was removed and the residue was dissolved in methanol (5 mL). Ether (50 mL) was added, the solution was cooled to -10° C., and the precipitate was filtered off, washed with ether, and air dried to give 1.2 g of (-) 5-amino-5,6-dihydro-4H-imidazo(4,5,1-ij)quinolin-2(1H)-one trifluoroacetate, mp 247° C. (α)DMeOH -18 °. Anal. Calc'd for C10H11N3O·C2HF3O2 : C, 47.53; H, 3.99; F, 18.80; N, 13.97. Found: C, 47.31; H, 4.26; F, 17.37; N, 13.48.

Workup

  1. customThe solvent was removed
  2. customthe residual oil was partitioned between chloroform and sodium hydroxide solution
  3. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-ed05706cf6fe40e49f45b23871cf8d9c
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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