Dichloromethane → HCID 22388593, compound

HRID 1072679Notes

Reaction equation

HRID 1072679 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:33])[CH2:25][NH:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:42]>C(OCC)C>[ClH:42].[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:33])[CH2:25][NH:26][S:27]([CH:30]([CH3:31])[CH3:32])(=[O:29])=[O:28])=[CH:19][CH:18]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 10227464HCID 10227464, compound

Product 1

HCID 22388593HCID 22388593, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(tert-Butoxy)-N-(2-{4-[4-(1-methyl-2-{[(methylethyl)sulfonyl]amino}ethoxy)phenyl]phenyl}ethyl)carboxamide (410 mg, 0.860 mmol, prepared in example 38), trifluoroacetic acid (0.86 mL), and methylene chloride (5.75 mL) were combined and stirred, by stirbar, in a 15 mL round bottom flask, in a nitrogen system, at room temperature, for one hour. The reaction mixture was then concentrated under reduced pressure, and dissolved in excess 5N sodium hydroxide, and extracted three times with 25 mL of methylene chloride. Next the organic extracts were combined, washed with 50 mL of water, dried with potassium carbonate, filtered, and concentrated under reduced vacuum, yielding 480 mg of crude material. This crude material was dissolved in diethyl ether, and anhydrous hydrogen chloride gas was bubbled through the solution, until it was acidic. Next, the acidic solution was allowed to stir, by stirbar, for an additional hour, and then was vacuum filtered, capturing the white precipitate and drying it in a vacuum oven at 40° C. for 30 minutes, yielding the title compound (305 mg, 94%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutiondissolved in excess 5N sodium hydroxide
  3. extractionextracted three times with 25 mL of methylene chloride
  4. washwashed with 50 mL of water
  5. dry with materialdried with potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced vacuum
  8. customyielding 480 mg of crude material
  9. customanhydrous hydrogen chloride gas was bubbled through the solution, until it
  10. stirringto stir, by stirbar, for an additional hour
  11. filtrationfiltered
  12. customdrying it in a vacuum oven at 40° C. for 30 minutes

Sources & evidence

ORD record
ord-66d43528bf93475dbe09574258e3ae0d
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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