Ethyl Acetate → HCID 86635773, compound

HRID 2426249Notes

Reaction equation

HRID 2426249 reaction equation
[CH3:1][N:2]1[C@@:6]2([CH2:37][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:8]=3[CH2:7]2)[N:15]=[C:14]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[C:27]([N+:28]([O-])=O)[C:22]=3[N:21]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:20]2=[O:36])[CH:13]=[CH:12]4)[C:5](=[O:38])[NH:4][C:3]1=[O:39].CCOC(C)=O>CO.[Pd]>[NH2:28][C:27]1[C:22]2[N:21]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:20](=[O:36])[N:19]([CH2:18][C:14]3[CH:13]=[CH:12][C:11]4[C:16](=[CH:17][C:8]5[CH2:7][C@@:6]6([C:5](=[O:38])[NH:4][C:3](=[O:39])[N:2]6[CH3:1])[CH2:37][C:9]=5[CH:10]=4)[N:15]=3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86635774HCID 86635774, compound

Product 1

HCID 86635773HCID 86635773, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of methyl (3-{[(7R)-3′-methyl-2′,5′-dioxo-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4′-imidazolidin]-2-yl]methyl}-7-nitro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate from Step A (143 mg, 0.27 mmol) and 10% Pd/C (20 mg) was stirred vigorously in MeOH (3 mL) and EtOAc (5 mL) under an atmosphere of hydrogen (ca. 1 atm). Additional amounts of 10% Pd/C (20 mg) were added after 16 h and 24 h. After a total reaction time of 96 h, the mixture was filtered through a pad of Celite, washing with MeOH, and the filtrate was concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z 501 (M+1).

Workup

  1. filtrationAfter a total reaction time of 96 h, the mixture was filtered through a pad of Celite
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-88dbaccee290432cac42a73c0ba0208a
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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