1-Naphthaleneacetic Acid → HCID 178427790, compound

HRID 1793189Notes

Reaction equation

HRID 1793189 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([C@@H:9]2[CH2:12][C@H:11]([O:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10]2)[CH:8]=1)([O-])=O.CCN(CC)CC.[C:31]1([CH2:41][C:42](O)=[O:43])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1>C(OCC)(=O)C.[Pd]>[C:31]1([CH2:41][C:42]([NH:1][C:4]2[N:5]=[CH:6][N:7]([C@H:9]3[CH2:12][C@H:11]([O:13][S:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[CH2:10]3)[CH:8]=2)=[O:43])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 68621-Naphthaleneacetic AcidHCID 8471TriethylamineHCID 178427791HCID 178427791, compound

Product 1

HCID 178427790HCID 178427790, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

trans-Toluene-4-sulfonic acid 3-(4-nitro-imidazol-1-yl)-cyclobutyl ester (Preparation 4, Step 2; 590 mg, 1.75 mmol) was mixed with 10% Pd on carbon (500 mg) in ethyl acetate (30 mL). The mixture was then reacted under 50 psi H2 at room temperature for 6 h. The mixture was filtered through celite into a flame-dried flask which was kept under a nitrogen atmosphere. Et3N (1.22 mL, 8.75 mmol) was added followed by 1-naphthylacetic acid (326 mg, 1.75 mmol) and tripropylphosphonic anhydride (1.1 mL, 1.7 M solution in ethyl acetate, 1.75 mmol). The mixture was stirred at room temperature for 1 h and was then diluted with ethyl acetate and was washed with water and brine. The organic layer was dried (MgSO4), was filtered, and was concentrated in vacuo. The resulting residue was purified by silica gel chromatography (50:1 chloroform-methanol) to afford 600 mg (72% yield) of trans-toluene-4-sulfonic acid 3-[4-(2-naphthalen-1-yl-acetylamino)-imidazol-1-yl]-cyclobutyl ester; 1H NMR (400 MHz, CDCl3) δ 7.9 (m, 2H), 7.85 (m, 2H), 7.76 (d, J=8.3 Hz, 2H), 7.48 (m, 2H), 7.42 (m, 2H), 7.33 (m, 2H), 7.04 (s, 1H), 4.96 (m, 1H), 4.73 (m, 1H), 2.7 (m, 4H), 2.44 (s, 3H); MS (AP/CI): 476.2 (M+H)+.

Workup

  1. customThe mixture was then reacted under 50 psi H2 at room temperature for 6 h
  2. filtrationThe mixture was filtered through celite into a flame-dried flask which
  3. washwas washed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationwas filtered
  6. concentrationwas concentrated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography (50:1 chloroform-methanol)

Sources & evidence

ORD record
ord-513e4b24fd25466eb922d5cf54934be7
Source dataset
uspto-grants-2006_07
Patent number
US07078529B2

Reaction notes

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