Isopropylamine → 5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(1-methylethyl)-1H-benzimidazol-2-amine

HRID 2227215Notes

Reaction equation

HRID 2227215 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].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]([CH3:3])[CH3:2])=[N:7][C:8]=2[CH:22]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 5129192-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 220862685,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(1-methylethyl)-1H-benzimidazol-2-amineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure V, isopropylamine (Aldrich, 3 mL, 34.92 mmol), and 2-bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (200 mg, 0.52 mmol) were reacted for 16 h. Purification on a silica gel column with 1:15 methanol:CH2Cl2 gave 5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(1-methylethyl)-1H-benzimidazol-2-amine (168 mg, 0.47 mmol, 90%); MS (EI): m/z (rel. intensity) 360 (0.17, M+); 1H NMR (DMSO-d6) δ7.41 (s, 1H, Ar—H), 7.32 (s,1H, Ar—H), 6.63 (d; 1H, NH, J=7.3 Hz), 5.73 (d, 1H, CH, J=6.6 Hz), 5.26 (m, 2H, 2 overlapping OH), 4.33 (m, 1H, CH), 4.01 (m, 1H, CH), 3.91 (m, 1H, CH), 3.81 (m, 1H, CH), 1.37 (d, 3H, CH3, J=6.1 Hz), 1.21 (d, 6H, CH3, J=6.3 Hz).

Workup

  1. customwere reacted for 16 h
  2. customPurification on a silica gel column with 1:15 methanol

Sources & evidence

ORD record
ord-cf9c2256998f40ffa4a64b1dbc7ce8bf
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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