Isopropylamine → HCID 56627375, compound

HRID 1734657Notes

Reaction equation

HRID 1734657 reaction equation
C([O:4][C@@H:5]1[C@@H: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][C@@H:7]([CH2:22][O:23]C(=O)C)[C@@H:6]1[O:27]C(=O)C)(=O)C.[CH:31]([NH2:34])([CH3:33])[CH3:32]>C(O)C>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]2[N:10]([C@@H:9]3[C@@H:5]([OH:4])[C@@H:6]([OH:27])[C@H:7]([CH2:22][OH:23])[CH2:8]3)[C:11]([NH:34][CH:31]([CH3:33])[CH3:32])=[N:12][C:13]=2[CH:18]=1

Participants

4

Reactant 2

HCID 6363Isopropylamine2×HCID 15407222HCID 15407222, compound

Product 1

HCID 56627375HCID 56627375, compound

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 (1.00 g, 1.92 mmole) was refluxed in ethanol (10 mL) with isopropylamine (1.6 mL, Fluka) under nitrogen for 24 hours. A second portion of isopropylamine (0.80 mL) was added and reflux continued for an additional 4 hours. Volatiles were evaporated, the residue was redissolved in ethanol, 1N sodium hydroxide (1.90 mL) was added, and volatiles were reevaporated. The residue was chromatographed on a silica gel column. Title compound was eluted with 10% methanol-ethyl acetate as a colorless glass. Concentration of an ethanol solution gave title compound as a off-white solid foam (360 mg, 46%). Such a sample was solidified by trituration with 95% water-5% methanol to give title compound as white powder (96%), m.p. 137°-138° C.; 1H-NMR(DMSO-d6)δ: 7.60 and 7.39 (both s, 2, aromatic CH), 6.64 (d, J=7.4 Hz, 1, NH), 5.14 (t, J=4.3 Hz, 1, OH), 4.81 (d, J=7.3 Hz, 1, OH), 4.70 (d, J=3.5 Hz, 1, OH), 4.70-4.50 (m, 1, NCH), 4.50-4.30 (m, 1, OCH), 4.10-4.00 (m, 1, NCH of cyclopropylamino), 3.9-3.75 (m, 1, OCH), 3.70-3.50 (m, 2, OCH2), 2.20-1.80 (m, 3, CH2 and CH of cyclopentane), 1.24 (d, J=6.6 Hz, 6, 2 CH3); mass spectrum (CI): 374(M+1); [α]20589 -3.72°, [α]20578 -2.60°, [α]20546 -2.23°, [α]20436 -9.67°, [α]20365 -51.7° (c=0.269, methanol).

Workup

  1. temperaturereflux
  2. customVolatiles were evaporated
  3. dissolutionthe residue was redissolved in ethanol
  4. addition1N sodium hydroxide (1.90 mL) was added
  5. customvolatiles were reevaporated
  6. customThe residue was chromatographed on a silica gel column
  7. washTitle compound was eluted with 10% methanol-ethyl acetate as a colorless glass

Sources & evidence

ORD record
ord-195b652b4e1a441daed07dcd27b1bc3c
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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