Hydrochloric Acid → HCID 136176847, compound

HRID 448680Notes

Reaction equation

HRID 448680 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:12]3[F:19])[C:6]=2[N:7]=1.Cl.[OH-:22].[Na+]>>[NH2:1][C:2]1[NH:3][C:4](=[O:22])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:12]3[F:19])[C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86586076HCID 86586076, compound

Product 1

HCID 136176847HCID 136176847, compound

Procedure

A mixture of the compound from Step I (4 mg, 0.08 mmol) in 2N aqueous NaOH (1.2 mL) was stirred at reflux temperature for 1.5 h. The solution was cooled in an ice-bath, neutralized with 2 N aqueous HCl and evaporated to dryness. The residue was suspended in MeOH, mixed with silica gel and evaporated. The solid residue was placed onto a silica gel column (packed in a solvent system of CH2Cl2/MeOH: 10/1) which was eluted with a solvent system of CH2Cl2/MeOH: 10/1. The fractions containing the product were collected and evaporated to dryness to yield the title compound (20 mg) as a white solid. 1H NMR (CD3OD): δ 3.73, 3.88 (2dd, 2H, J=12.4, 3.8, 2.6 Hz), 4.01 (m, 1H), 4.47 (ddd, 1H J=16.5, 6.6 Hz), 5.14 (ddd, 1H, J=5.3, 4.7 Hz), 6.19 (dd, 1H, J=17.8, 3.0 Hz), 6.39 (d, 1H, J=3.6 Hz), 6.95 (d, 1H).

Workup

  1. temperatureat reflux temperature for 1.5 h
  2. temperatureThe solution was cooled in an ice-bath
  3. customevaporated to dryness
  4. additionmixed with silica gel
  5. customevaporated
  6. wash10/1) which was eluted with a solvent system of CH2Cl2/MeOH
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-16794299b7ac44e4a1973748319b6266
Source dataset
uspto-grants-2013_07
Patent number
US08481712B2

Reaction notes

Loading…