Hydrochloric Acid → HCID 21256672, compound

HRID 635969Notes

Reaction equation

HRID 635969 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][N:15](C(OC=C)=O)[CH2:14][C:13]=3[NH:12][C:11]3[CH2:25][CH2:26][CH2:27][C:28](=[O:29])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:30]>C(O)C>[ClH:30].[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][NH:15][CH2:14][C:13]=3[NH:12][C:11]3[CH2:25][CH2:26][CH2:27][C:28](=[O:29])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18000954HCID 18000954, compound

Product 1

HCID 21256672HCID 21256672, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from Example 2B (0.25 g) in ethyl alcohol (20 mL) was treated with 6M HCl (20 mL) and heated to reflux for 1.5 hours. The ethyl alcohol was evaporated and the aqueous portion basified with 1N sodium hydroxide. The basified solution was extracted with methylene chloride (3x). The combined methylene chloride extractions were concentrated and the residue was purified by flash chromatography over silica gel (10:90:1 ethanol/methylene chloride/saturated ammonium hydroxide) to provide the title compound (0.10 g) which was converted to the hydrochloride salt.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. customThe ethyl alcohol was evaporated
  4. extractionThe basified solution was extracted with methylene chloride (3x)
  5. extractionThe combined methylene chloride extractions
  6. concentrationwere concentrated
  7. customthe residue was purified by flash chromatography over silica gel (10:90:1 ethanol/methylene chloride/saturated ammonium hydroxide)

Sources & evidence

ORD record
ord-b1bcbdceeff9405cbe83d4e5548672d1
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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