Benzoyl chloride → HCID 59289350, compound

HRID 2191033Notes

Reaction equation

HRID 2191033 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:11]3[C@@H:15]4[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]4[C@@H:13]([CH2:21][OH:22])[O:12]3)[N:9]=[CH:10][C:3]=12.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[OH:22][CH2:21][C@@H:13]1[C@H:14]2[O:18][C:17]([CH3:19])([CH3:20])[O:16][C@H:15]2[C@H:11]([N:8]2[C:4]3=[N:5][CH:6]=[N:7][C:2]([NH:1][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:3]3[CH:10]=[N:9]2)[O:12]1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 59289319((3aR,4R,6R,6aR)-6-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Product 1

HCID 59289350HCID 59289350, compoundYield 49%

Procedure

Compound 22.2 (4.20 g, 13.66 mmol) in pyrdine (40 mL, 0.33 M) was cooled to 0° C. and treated with benzoyl chloride (12.68 mL, 109.3 mmol) The mixture was warmed to room temperature and stirred for 16 h. The solvent was removed in vacuo and the residue was treated with 2.5 N KOH (40 mL) in pyridine (40 mL) and stirred for 20 min. The mixture was cooled to 0° C. and AcOH was added (6 mL). The solvent was removed in vacuo and the residue was dissolved in EtOAc (150 mL) and washed with H2O (100 mL), saturated NaHCO3 (2×100 mL), and brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford compound 22.3 (2.74 g, 49% yield) as a white solid: 1H NMR (CDCl3, 300 MHz) 9.02 (br s, 1H), 8.80 (s, 1H), 8.55 (s, 1H), 7.97 (d, J=7.5 Hz, 2H), 7.62 (app t, J=7.5 Hz, 1H), 7.52 (t, J=7.5 Hz, 2H), 6.65 (s, 1H), 5.25 (m, 1H), 5.07 (d, J=6.0 Hz, 1H), 4.99 (br s, 1H), 4.53 (m, 1H), 3.91 (m, 1H), 3.77 (m, 1H), 1.61 (s, 3H), 1.35 (s, 3H); MS (ESI) m/z 412 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with 2.5 N KOH (40 mL) in pyridine (40 mL)
  3. stirringstirred for 20 min
  4. temperatureThe mixture was cooled to 0° C.
  5. additionAcOH was added (6 mL)
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residue was dissolved in EtOAc (150 mL)
  8. washwashed with H2O (100 mL), saturated NaHCO3 (2×100 mL), and brine (100 mL)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-721ab5d1670644c882d8ca5c1e709e57
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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