Cyclobutylamine → HCID 54372919, compound

HRID 1734660Notes

Reaction equation

HRID 1734660 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.[CH:31]1([NH2:35])[CH2:34][CH2:33][CH2:32]1>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]([NH:35][CH:31]3[CH2:34][CH2:33][CH2:32]3)=[N:12][C:13]=2[CH:18]=1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 54404171HCID 54404171, compound

Product 1

HCID 54372919HCID 54372919, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

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 absolute ethanol (7 mL) and cyclobutylamine (0.41 mL, 4.8 mmol) was added. The solution was refluxed under nitrogen for 18 hours. Volatiles were evaporated and the residue stirred in methanol half-saturated with ammonia at 0° C. (20 mL) for 18 hours. Volatiles were removed in vacuo and the residue crystallized from ethanol-water to give title compound as white solid, m.p. 250° C. dec.; 1H-NMR(DMSO-d6)δ: 7.61 and 7.38 (both s, 1 each, aromatic CH), 7.07 (d, J=7.4 Hz, 1, NH), 5.15 (t, J=3.9 Hz, 1, OH), 4.81 (d, J=7.3 Hz, 1, OH), 4.71-4.45 (m overlapping d at 4.71, J=3.5 Hz, total 2, OH and NCH), 4.40-4.30 (m, 2. OCH and NCH), 3.82-3.80 (m, 1, OCH), 3.72-3.42 (both m, 1 each, OCH2), 2.32-1.67 (three m, 9, 4CH2 and CH); mass spectrum (CI): 386(M +1).

Workup

  1. temperatureThe solution was refluxed under nitrogen for 18 hours
  2. customVolatiles were evaporated
  3. customVolatiles were removed in vacuo
  4. customthe residue crystallized from ethanol-water

Sources & evidence

ORD record
ord-515c5540ef39402aace7ce5b2a41928a
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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