Hydrochloric Acid → HCID 68536240, compound

HRID 1816954Notes

Reaction equation

HRID 1816954 reaction equation
[CH3:1][C@H:2]([NH:9][C:10]([NH:12][C:13]1[N:28]=[C:16]2[N:17]=[CH:18][CH:19]=[C:20]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[N:15]2[N:14]=1)=[O:11])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[N:29]1([CH2:35][CH2:36]O)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[ClH:69]>C(Cl)Cl.CO>[ClH:69].[CH3:1][C@H:2]([NH:9][C:10]([NH:12][C:13]1[N:28]=[C:16]2[N:17]=[CH:18][CH:19]=[C:20]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:36][CH2:35][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:25][CH:26]=3)[N:15]2[N:14]=1)=[O:11])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 135507469HCID 135507469, compound2×

Product 1

HCID 68536240HCID 68536240, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-1-(1,5-dimethylhexyl)-3-[7-(4-hydroxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]urea (the compound obtained in Example 255; 20 mg) was dissolved in methylene chloride (1 ml) in an argon atmosphere. Thereafter, 2-morpholin-4-ylethanol (21 mg) and triphenylphosphine (41 mg) were added to the obtained solution, and the obtained mixture was stirred at a room temperature for 30 minutes. Thereafter, the reaction solution was cooled on ice, and diethyl azodicarboxylate (27 mg) was then added thereto, followed by stirring the mixture at the same temperature for 30 minutes. The reaction solution was further stirred at a room temperature overnight. Thereafter, the reaction solution was concentrated under a reduced pressure. Thereafter, ethyl acetate (3 ml) and 1 M hydrochloric acid (3 ml) were added thereto, and the obtained mixture was separated. After the obtained water layer was washed with ethyl acetate (3 ml), an aqueous 6 M sodium hydroxide solution was added thereto to convert the solution to be alkaline. After extraction with methylene chloride (5 ml), the organic layer was washed with distilled water (5 ml×2), and the solvent was then distilled off under a reduced pressure. The residue was washed by suspension in a mixed solvent (2 ml) consisting of 50% ethyl acetate and hexane to obtain the captioned compound in the form of a free body (18 mg). Thereafter, methanol (1 ml) and 1 M hydrochloric acid (0.2 ml) were added to the obtained compound and dissolved therein, and the obtained mixture was then concentrated under a reduced pressure. The obtained residue was washed by suspension in acetone (0.5 ml) to obtained the captioned compound (17 mg).

Workup

  1. additionwas then added
  2. stirringby stirring the mixture at the same temperature for 30 minutes
  3. stirringThe reaction solution was further stirred at a room temperature overnight
  4. concentrationThereafter, the reaction solution was concentrated under a reduced pressure
  5. additionThereafter, ethyl acetate (3 ml) and 1 M hydrochloric acid (3 ml) were added
  6. customthe obtained mixture was separated
  7. washAfter the obtained water layer was washed with ethyl acetate (3 ml)
  8. additionan aqueous 6 M sodium hydroxide solution was added
  9. extractionAfter extraction with methylene chloride (5 ml)
  10. washthe organic layer was washed with distilled water (5 ml×2)
  11. distillationthe solvent was then distilled off under a reduced pressure
  12. washThe residue was washed by suspension in a mixed solvent (2 ml)
  13. customto obtain the captioned compound in the form of a free body (18 mg)
  14. dissolutiondissolved
  15. concentrationthe obtained mixture was then concentrated under a reduced pressure
  16. washThe obtained residue was washed by suspension in acetone (0.5 ml)

Sources & evidence

ORD record
ord-05ff1b8f87524c449e40a247f2b791ac
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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