Hydrochloric Acid → HCID 86592753, compound

HRID 1825686Notes

Reaction equation

HRID 1825686 reaction equation
C(N1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[O:21][C:22]4[C:27]([C:28](=[O:30])[CH:29]=3)=[CH:26][C:25]([F:31])=[CH:24][C:23]=4[N:32]3[CH2:37][CH2:36][N:35](C)[CH2:34][CH2:33]3)=[O:19])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=O)CC.ClC(OC(Cl)C)=[O:41].[Na+].[I-].Cl>C(Cl)(Cl)Cl.ClCCCl>[N:8]1([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[O:21][C:22]4[C:27]([C:28](=[O:30])[CH:29]=3)=[CH:26][C:25]([F:31])=[CH:24][C:23]=4[N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[O:19])=[CH:13][CH:12]=2)[CH2:7][CH2:6][O:41][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 5213051-Chloroethyl chloroformateHCID 9830790442548-99-4

Product 1

HCID 86592753HCID 86592753, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Dry 6-flouro-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid [4-(4-propionyl-piperazin-1-yl)-phenyl]-amide (Example 72)(1 g 1.9 mmol) was added to 100 mL of rigorously dried 1,2-dichloroethane in a flask under N2 atmosphere and magnetic stirring. The mixture was cooled to 0° C. and freshly distilled 1-chloroethyl chloroformate (650 ul, 858 mg, 6 mmol, 3 eq) was added drop wise. The reaction was then heated under reflux for 5 hours at which time LC/MS revealed complete consumption of starting material. NaI (1 g, 1 eq) was added and heating continued for 2 days more. The reaction was then allowed to cool and filtered and evaporated to dryness under reduced pressure. MeOH (100 mL) was added and heated to reflux for 4 h, filtered hot and evaporated to dryness. The product was isolated by chromatography using silica gel and CHCl3/5% MeOH as an eluent. This gave 700 mg of the product HCl salt as a yellow solid. LCMS−m/z=508.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureunder reflux for 5 hours at which time LC/MS
  3. customconsumption of starting material
  4. temperatureheating
  5. temperatureto cool
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. additionMeOH (100 mL) was added
  9. temperatureheated
  10. temperatureto reflux for 4 h
  11. filtrationfiltered hot
  12. customevaporated to dryness
  13. customThe product was isolated by chromatography

Sources & evidence

ORD record
ord-8753a786222e4e63bba49626669dc652
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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