HCID 57291959, compound → HCID 70177973, compound

HRID 2227193Notes

Reaction equation

HRID 2227193 reaction equation
Cl[C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH3:14])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:4]=2[N:3]=1>C(O)C.C(N)(C)C>[CH3:20][O:19][C:17]1[CH:16]=[CH:15][C:5]2[N:6]([C@@H:7]3[O:13][C@H:12]([CH3:14])[C@@H:10]([OH:11])[C@H:8]3[OH:9])[C:2]([NH:3][CH:4]([CH3:18])[CH3:5])=[N:3][C:4]=2[CH:18]=1

Participants

4

Reactant 1

HCID 57291959HCID 57291959, compound

Product 1

HCID 70177973HCID 70177973, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6363IsopropylamineSolvent

Procedure

2-Chloro-5-methoxy-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (0.320 g, 1.1 mmol) was dissolved in ethanol (15 mL) and isopropylamine (5 mL). The resulting mixture was heated in a sealed tube for three days, after which time it was concentrated in vacuo. The resulting product was purified by flash chromatography (9:0.5:0.5 CH2Cl2:ethyl acetate:methanol) to yield the title compound (18 mg, 5%) as a 1.5:1 mix of regioisomers by 1H NMR; MS (ES): m/z 322 (M+1); 1H NMR (DMSO-d6) δ: 7.13 (d, J=8.5 Hz, 0.4H), 7.03 (d, J=8.5, 0.6H), 6.85 (d, J=2.4 Hz, 0.6H), 6.76 (d, J=2.4 Hz, 0.4H), 6.62 (dd, 0.4H), 6.50 (dd, 0.6H), 5.67 (t, 1H), 5.28-5.19 (m, 1.5H), 4.37 (m, 1H), 3.73 (s, 3H), 1.40 (m, 3H), 1.23 (d, 6H).

Workup

  1. temperatureThe resulting mixture was heated in a sealed tube for three days
  2. concentrationafter which time it was concentrated in vacuo
  3. customThe resulting product was purified by flash chromatography (9:0.5:0.5 CH2Cl2:ethyl acetate:methanol)

Sources & evidence

ORD record
ord-6b406fe0888e43ae85340ddbcb41521f
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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