Cyclopropylamine → HCID 54074863, compound

HRID 1734659Notes

Reaction equation

HRID 1734659 reaction equation
C([O:4][CH:5]1[CH2:9][CH:8]([CH2:10][O:11]C(=O)C)[CH2:7][CH:6]1[N:15]1[C:19]2[CH:20]=[C:21]([Cl:25])[C:22]([Cl:24])=[CH:23][C:18]=2[N:17]=[C:16]1Br)(=O)C.[CH:27]1([NH2:30])[CH2:29][CH2:28]1>>[CH:27]1([NH:30][C:16]2[N:15]([CH:6]3[CH2:7][CH:8]([CH2:10][OH:11])[CH2:9][CH:5]3[OH:4])[C:19]3[CH:20]=[C:21]([Cl:25])[C:22]([Cl:24])=[CH:23][C:18]=3[N:17]=2)[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 67613748HCID 67613748, compound

Product 1

HCID 54074863HCID 54074863, compound

Procedure

(±)-(1R*, 2R*, 4S*)-4-(Acetoxymethyl)-2-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-cyclopentyl acetate (500 mg, 1.50 mmol) was reacted with cyclopropylamine (0.73 mL) in the manner of Example 74. Crude product was chromatographed on silica gel and title compound eluted with 5% methanol-ethyl acetate as a colorless glass which solidified from ethyl acetate-hexanes to white powder (180 mg, 48%), m.p. 251°-253° C.; 1H-NMR(DMSO-d6)δ: 7.54 and 7.45 (both s, 2, aromatic CH), 5.04 (d, J=5.1 Hz, 1, OH), 4.97 (t, J=4.7 Hz, 1, OH), 4.60-4.50 and 4.50-4.30 (both m, 1 each, NCH and OCH), 3.50 (m, 2, OCH2), 2.80 (m, 1, CH), 2.35-2.10 (m, 1, CH), 2.05-1.80 (m, 3, CH2 and CH of cyclopentane), 1.80-1.60 (m, 1, CH), 0.80-0.50 (1 m, 4, 2CH2 of cyclopropyl); mass spectrum (CI): 356 (M+1).

Workup

  1. customCrude product was chromatographed on silica gel and title compound
  2. washeluted with 5% methanol-ethyl acetate as a colorless glass which

Sources & evidence

ORD record
ord-16d1ae1bb8b348429f4d099bb12aea1e
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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