2,4-Difluoroaniline → HCID 69827764, compound

HRID 2297663Notes

Reaction equation

HRID 2297663 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([C@@H:10]2[C@@H:14]3[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]3[C@H:12]([N:20]3[CH:28]=[N:27][C:26]4[C:21]3=[N:22][CH:23]=[N:24][C:25]=4ON3C4C=CC=CC=4N=N3)[O:11]2)[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:39][C:40]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:41]=1[NH2:42]>>[C:1]([C:5]1[N:9]=[C:8]([C@@H:10]2[C@@H:14]3[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]3[C@H:12]([N:20]3[CH:28]=[N:27][C:26]4[C:21]3=[N:22][CH:23]=[N:24][C:25]=4[NH:42][C:41]3[CH:43]=[CH:44][C:45]([F:47])=[CH:46][C:40]=3[F:39])[O:11]2)[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 97092,4-DifluoroanilineHCID 69827476HCID 69827476, compound

Product 1

HCID 69827764HCID 69827764, compound

Conditions

Temperature
80 °C

Procedure

9-{(3aR,4R,6S,6aR)-6-[3-(tert-butyl)-1,2,4-oxadiazol-5-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-6-(1H-1,2,3-benzotriazol-1-yloxy)-9H-purine (50 mg) was dissolved in 2,4-difluoroaniline (0.4 ml) and the mixture heated at 80° C. for 96 h. The mixture was then cooled to 20° C. and partitioned between dichloromethane (25 ml) and 1 M hydrochloric acid (15 ml). The separated aqueous phase was further extracted with dichloromethane (1×25 ml) and the combined organic extracts were evaporated to dryness in vacuo. Purification by automated preparative HPLC afforded the title compound (18.3 mg) as a dark purple gum.

Workup

  1. temperatureThe mixture was then cooled to 20° C.
  2. custompartitioned between dichloromethane (25 ml) and 1 M hydrochloric acid (15 ml)
  3. extractionThe separated aqueous phase was further extracted with dichloromethane (1×25 ml)
  4. customthe combined organic extracts were evaporated to dryness in vacuo
  5. customPurification by automated preparative HPLC

Sources & evidence

ORD record
ord-1c84c65aafc7429a8aaab6d42ea8c7a5
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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