4-Chloro-2-fluoroaniline → HCID 86588186, compound

HRID 2297682Notes

Reaction equation

HRID 2297682 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]#[CH:15])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2ON1C2C=CC=CC=2N=N1)(=[O:3])[CH3:2].[F:35][C:36]1[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:37]=1[NH2:38]>>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]#[CH:15])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH:38][C:37]1[CH:39]=[CH:40][C:41]([Cl:43])=[CH:42][C:36]=1[F:35])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 938984-Chloro-2-fluoroanilineHCID 18336821HCID 18336821, compound

Product 1

HCID 86588186HCID 86588186, compound

Conditions

Temperature
60 °C

Procedure

(2R,3R,4R,5R)-4-(acetyloxy)-2-[6-(1H-1,2,3-benzotriazol-1-yloxy)-9 H-purin-9-yl]-5-ethynyltetrahydrofuran-3-yl acetate was treated with 2-fluoro-4-chloroaniline (0.63 ml), and the mixture was heated at 60° C. for 22.5 h. The mixture was purified by chromatography on silica gel (Varian Bondelut cartridge), eluting with ethyl acetate:cyclohexane 10:90-60:40, to give the title compound (55 mg).

Workup

  1. customThe mixture was purified by chromatography on silica gel (Varian Bondelut cartridge)
  2. washeluting with ethyl acetate:cyclohexane 10:90-60:40

Sources & evidence

ORD record
ord-f6ab49fc28af4caaba07171e311138f7
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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