Hydrochloric Acid → HCID 135482165, compound

HRID 1245489Notes

Reaction equation

HRID 1245489 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([CH2:11][CH3:12])=[CH:9][N:8]([C@@H:13]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:14]3[OH:15])[C:6]=2[N:7]=1.Cl.[OH-:24].[Na+]>>[NH2:1][C:2]1[NH:3][C:4](=[O:24])[C:5]2[C:10]([CH2:11][CH3:12])=[CH:9][N:8]([C@@H:13]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:14]3[OH:15])[C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 60104726HCID 60104726, compound

Product 1

HCID 135482165HCID 135482165, compound

Procedure

A mixture of the compound from Step B (104 mg, 0.32 mmol) in 2N aqueous NaOH (10 mL) was stirred at reflux temperature for 15 min. 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 (48 mg) as a white solid.

Workup

  1. temperatureat reflux temperature for 15 min
  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-bebf3e30b2284396a47e9794dee8b412
Source dataset
uspto-grants-2006_10
Patent number
US07125855B2

Reaction notes

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