Hydrochloric Acid → HCID 135409309, compound

HRID 1836211Notes

Reaction equation

HRID 1836211 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:6]=2[N:7]=1.Cl.[OH-:23].[Na+]>>[NH2:1][C:2]1[NH:3][C:4](=[O:23])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9944695HCID 9944695, compound

Product 1

HCID 135409309HCID 135409309, compound

Procedure

A mixture of intermediate from Step B (100 mg, 0.32 mmol) in 2N aqueous NaOH (20 mL) was stirred at reflux temperature for 1.5 h. The solution was cooled in 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 mixture of CH2Cl2/MeOH: 10/1) which was eluted with a solvent system of CH2Cl2/MeOH: 10/1 and 5/1. The fractions containing the product were collected and evaporated to dryness to yield the title compound (90 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-5e36959c76864020acdb52a3bced4963
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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