Isopropylamine → HCID 56627375, compound

HRID 1416438Notes

Reaction equation

HRID 1416438 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, 1 N 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 20 589-3.72°, [α]20 578-2.60°, [α]20 546-2.23°, [α]20 436-9.67°, [α]20 365-51.7 ° (c=0.269, methanol). [See Examples 16-18 and 20]

Workup

  1. temperaturereflux
  2. customVolatiles were evaporated
  3. dissolutionthe residue was redissolved in ethanol
  4. addition1 N 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-892811dcbb9e4c0999df39795c37c200
Source dataset
uspto-grants-1999_06
Patent number
US05912356

Reaction notes

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