Sodium Hydroxide → HCID 54441857, compound

HRID 1734662Notes

Reaction equation

HRID 1734662 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]([CH3:22])[CH:6]1[O:23]C(=O)C)(=O)C.[CH:27]1([NH2:30])[CH2:29][CH2:28]1.[OH-].[Na+]>COC(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:23])[CH:7]([CH3:22])[CH2:8]3)[C:11]([NH:30][CH:27]3[CH2:29][CH2:28]3)=[N:12][C:13]=2[CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 54317220HCID 54317220, compound

Product 1

HCID 54441857HCID 54441857, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

(±)-(1R*, 2S*, 3R*, 5S*)-5-(2-Bromo-5,6-dichloro-1H-benzimidazol-1-yl)-3-methyl-1,2-cyclopentanediyl diacetate (Part D, 350 mg, 0.75 mmole) and cyclopropylamine (Aldrich, 0.53 mL) were refluxed in methoxyethanol (5 mL) for 5 hours. 1N sodium hydroxide (0.75 mL) was added to the cooled reaction mixture and volatiles were evaporated in vacuo. The residue was chromatographed on silica gel. Product was eluted with 5% methanol-chloroform. Recrystallization from methanol-ethyl acetate gave (±)-(1R*, 2S*, 3R*, 5S*)-5-[5,6-dichloro-2-(cyclopropylamino)-1H-benzimidazol-1-yl]-3-methyl-1,2-cyclopentanediol as white crystals (170 mg, 64%); m.p. 231°-233° C.; 1H-NMR(DMSO-d6)δ: 7.48 and 7.39 (both s, 1 each, 2 benzimidazole CH), 7.10 (m, 1, NH), 4.83 (d, J=5.9 Hz, 1, OH), 4.74 (d, J=5.1 Hz, 1, OH), 4.5-4.3 (m, 2, NCH and OCH), 3.7-3.6 (m, 1, OCH), 2.85-2.7 (m, 1, CHNH), 2.1-1.8 (m, 2, CH2 and CH), 1.7-1.5 (m, 1, CH), 1.16 (d, J=5.4 Hz, 3, CHCH3), 0.8-0.5 (m, 4, 2 CH2 of cyclopropyl); mass spectrum (CI): 356 (M+1).

Workup

  1. customwere evaporated in vacuo
  2. customThe residue was chromatographed on silica gel
  3. washProduct was eluted with 5% methanol-chloroform
  4. customRecrystallization from methanol-ethyl acetate

Sources & evidence

ORD record
ord-93d45603088b4661ae158ba0164263b8
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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