Cyclopropylamine → (2R,3R,4S,5R)-2-[5,6-dichloro-2-(cyclopropylamino)benzimidazol-1-yl]-5-methyl-tetrahydrofuran-3,4-diol

HRID 2227211Notes

Reaction equation

HRID 2227211 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Br[C:6]1[N:10]([C@@H:11]2[O:17][C@H:16]([CH3:18])[C@@H:14]([OH:15])[C@H:12]2[OH:13])[C:9]2[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:8]=2[N:7]=1>C(Cl)Cl>[Cl:23][C:21]1[C:20]([Cl:24])=[CH:19][C:9]2[N:10]([C@@H:11]3[O:17][C@H:16]([CH3:18])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[C:6]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[N:7][C:8]=2[CH:22]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 5129192-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 9798857(2R,3R,4S,5R)-2-[5,6-dichloro-2-(cyclopropylamino)benzimidazol-1-yl]-5-methyl-tetrahydrofuran-3,4-diolYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure V, cyclopropyl amine (Aldrich, 5 mL, 71.28 mmol), and 2-bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (250 mg, 0.65 mmol) reacted for 92 h. Purification on a silica gel column with 1:15 methanol:CH2Cl2 gave the title compound (120 mg, 0.33 mmol, 52%); MS (El): m/z (rel. intensity) 358 (0.08, M+); 1H NMR (DMSO-d6) δ7.48 (s, 1H, Ar—H), 7.35 (s, 1H, Ar—H), 7.13 (d, 1H, NH, J=2.0 Hz), 5.61 (d,1H, CH, J=6.6 Hz), 5.25 (m, 2H, 2 overlapping OH), 4.36 (m,1H, CH), 3.88 (m, 1H, CH), 3.79 (m, 1H, CH), 2.76 (m, 1H, CH), 1.36 (d, 3H, CH3, J=6.3 Hz), 0.70 (m, 2H, CH2), 0.53 (m, 2H, CH2).

Workup

  1. customreacted for 92 h
  2. customPurification on a silica gel column with 1:15 methanol

Sources & evidence

ORD record
ord-82feaa45949d4f5880aa6c480a15e8e0
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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