Ammonia → HCID 23516053, compound

HRID 1734661Notes

Reaction equation

HRID 1734661 reaction equation
C([O:4][CH:5]1[CH:9]([N:10]2[C:14]3[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=3[N:12]=[C:11]2Br)[CH2:8][CH:7]([CH2:22][O:23]C(=O)C)[CH:6]1[O:27]C(=O)C)(=O)C.[NH:31]1[CH2:34][CH2:33][CH2:32]1.N>C(O)C>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]2[N:10]([CH:9]3[CH:5]([OH:4])[CH:6]([OH:27])[CH:7]([CH2:22][OH:23])[CH2:8]3)[C:11]([N:31]3[CH2:34][CH2:33][CH2:32]3)=[N:12][C:13]=2[CH:18]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10422AzetidineHCID 54404171HCID 54404171, compound

Product 1

HCID 23516053HCID 23516053, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (500 mg, 0.958 mmol) was dissolved in ethanol (7 mL). Azetidine (Aldrich, 250 mg, 4.4 mmol as 98%) was added and the solution was refluxed under nitrogen for 48 hours. Methanolic ammonia (saturated at 0° C., 20 mL) was added to the cooled solution and this solution was stirred for an additional 18 hours. Volatiles were evaporated, the residue was redissolved in ethanol (10 mL) and 1N sodium hydroxide (0.96 mL) was added. Volatiles were evaporated and the residual solids were triturated with water (3 mL) and filtered. Resolidification of the solid from acetonitrile-methanol gave title compound as white powder (146 mg, 41%), m.p. 221°-222° C.; 1H-NMR(DMSO-d6)δ: 7.78 and 7.53 (both s, 1 each, 2 aromatic CH), 5.05 (t, J=4.3 Hz, 1, OH), 4.91 (d, J=5.3 Hz, 1, OH), 4.59 (d, J=3.7 Hz, 1, OH), 4.45-4.40 (m, 2, OCH and NCH), 4.25-4.15 (m, 4, 2 CH2N), 3.82-3.79 (m, 1, OCH), 3.66-3.43 (both m, 1 each, OCH2), 2.40-2.32 (m, 2, CH2), 2.03-1.95 (m, 3, CH2 and NCH); mass spectrum (CI): 372(M+1).

Workup

  1. temperaturethe solution was refluxed under nitrogen for 48 hours
  2. customVolatiles were evaporated
  3. dissolutionthe residue was redissolved in ethanol (10 mL)
  4. addition1N sodium hydroxide (0.96 mL) was added
  5. customVolatiles were evaporated
  6. customthe residual solids were triturated with water (3 mL)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-3500b1cf9557418ba8da98b5528c8f8c
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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