Ethanol → HCID 16057516, compound

HRID 381645Notes

Reaction equation

Cl.[CH2:2]([NH2:4])C.C(N(CC)CC)C.Br[C:13]1[N:17]([C@H:18]2[O:30][C@@H:29]([CH2:31][O:32]C(=O)C)[C@H:24]([O:25]C(=O)C)[C@@H:19]2[O:20]C(=O)C)[C:16]2[CH:36]=[C:37]([Cl:41])[C:38]([Cl:40])=[CH:39][C:15]=2[N:14]=1.C(O)C>CN(C=O)C>[Cl:40][C:38]1[C:37]([Cl:41])=[CH:36][C:16]2[N:17]([C@H:18]3[O:30][C@@H:29]([CH2:31][OH:32])[C@H:24]([OH:25])[C@@H:19]3[OH:20])[C:13]([NH:4][CH3:2])=[N:14][C:15]=2[CH:39]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethylamine hydrochloride (3.7 g, 46 mmol), triethylamine (7 mL), and 2-bromo-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (0.60 g, 1.1 mmol) were combined with absolute ethanol (20 mL) and stirred at 80° C. for 24 h. The reaction mixture was separated between saturated sodium bicarbonate (2×50 mL) and ethyl acetate (200 mL). The organics were dried with sodium sulfate, concentrated, and purified on a silica gel column (2.5×18 cm, 230-400 mesh) with 1:20 methanol:dichloromethane. The main product off the column was a white solid (0.30 g, 0.96 mmol, 87%) m.p. 155-157° C.; [a]20D=(−) 20.6 (c=0.5 DMF).

Workup

customThe reaction mixture was separated between saturated sodium bicarbonate (2×50 mL) and ethyl acetate (200 mL)
dry with materialThe organics were dried with sodium sulfate
concentrationconcentrated
custompurified on a silica gel column (2.5×18 cm, 230-400 mesh) with 1:20 methanol

Sources & evidence

ORD record: ord-24dd27b0c5d04398948a62e0c452d87f
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06307043B1

Reaction notes

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