Isopropylamine → HCID 57164492, compound

HRID 2227210Notes

Reaction equation

HRID 2227210 reaction equation
Br[C:2]1[N:6]([C@@H:7]2[O:12][C@H:11]([CH3:13])[C@@H:9]([OH:10])[C@H:8]2[F:14])[C:5]2[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:4]=2[N:3]=1.[CH:21]([NH2:24])([CH3:23])[CH3:22]>C(O)C>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:5]2[N:6]([C@@H:7]3[O:12][C@H:11]([CH3:13])[C@@H:9]([OH:10])[C@H:8]3[F:14])[C:2]([NH:24][CH:21]([CH3:23])[CH3:22])=[N:3][C:4]=2[CH:18]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 57137967HCID 57137967, compound

Product 1

HCID 57164492HCID 57164492, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-5,6-dichloro-1-(2,5-dideoxy-2-fluoro-beta-D-ribofuranosyl)-1H-benzimidazole (0.075 g, 0.2 mmoles) was heated in a solution of isopropylamine (Fluka, 2 mL) and absolute ethanol (6 mL) in a 90° C. oil bath for 18 hrs. The solvents were removed in vacuo. The residue was partitioned between water and ethyl acetate. The ethyl acetate solution was dried with MgSO4, filtered and solvent removed in vacuo to give the product (0.06 g) in 85% yield. MS (APCl+): m+1/z, 362; 1H NMR (DMSO-6) δ7.39 (s, 1H, Ar—H), 7.18 (s, 1H, Ar—H), 6.94 (d, 1H, NH, J=7 Hz), 6.09 (d, 1H, H-1′, J=19 Hz), 5.72 (d, 1H, OH-3′, J=6 Hz), 5.26 (d, 1H, H-2′, J=53 Hz), 3.9 (m, 3H,), 1.35 (d, 3H, H-5′, J=6 Hz), 1.18 (m, 6H, CH3).

Workup

  1. customThe solvents were removed in vacuo
  2. customThe residue was partitioned between water and ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried with MgSO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-d7d02fd80d1f40f6a579809aee04265b
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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