Hydrochloric Acid → HCID 58379073, compound

HRID 1951163Notes

Reaction equation

HRID 1951163 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[C@@H:20]([CH3:31])[CH2:19]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.Cl.CO>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([N:18]3[CH2:23][CH2:22][NH:21][C@@H:20]([CH3:31])[CH2:19]3)=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58378949HCID 58378949, compound

Product 1

HCID 58379073HCID 58379073, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Treat a solution of (S)-tert-butyl 4-(4-(4-fluorophenyl)phthalazin-1-yl)-2-methylpiperazine-1-carboxylate (7.05 g, 16.2 mmol) in 1,4-dioxane (50 mL) with 4 M HCl in 1,4-dioxane (25 mL). Add MeOH to dissolve the resultant precipitate and stir for 2 h at ambient temperature. Concentrate the reaction mixture under reduced pressure. Dissolve residue in MeOH and pour onto a 50 g Varian® SCX column. Rinse with MeOH and CH2Cl2, then elute the product with 1:1 CH2Cl2: 2 M ammonia in MeOH. Concentrate the eluent under reduced pressure to provide the title compound as a pale yellow foam (4.83 g, 93%). ES/MS m/z 323.2 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. additionDissolve residue in MeOH and pour onto a 50 g Varian® SCX column
  3. washRinse with MeOH and CH2Cl2
  4. washelute the product with 1:1 CH2Cl2
  5. concentrationConcentrate the eluent under reduced pressure

Sources & evidence

ORD record
ord-4ae9064dbb0d40fc81ec3de7d1803d2e
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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