Hydrochloric Acid → HCID 67345696, compound

HRID 1951165Notes

Reaction equation

HRID 1951165 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][NH:21][C@@H:20]([CH2:24][OH:25])[CH2:19]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1.[ClH:36]>C(Cl)Cl.CO>[ClH:36].[F:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([N:21]2[CH2:22][CH2:23][N:18]([C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9][N:10]=3)[CH2:19][C@@H:20]2[CH2:24][OH:25])=[O:35])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 709554-Fluorophenyl isocyanateHCID 58379032HCID 58379032, compound

Product 1

HCID 67345696HCID 67345696, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (R)-(4-(4-(4-fluorophenyl)phthalazin-1-yl)piperazin-2-yl)-methanol (0.15 g, 0.44 mmol) in CH2Cl2 (3 ml) with 1-fluoro-4-isocyanatobenzene (0.04 g, 0.31 mmol). Stir the reaction at ambient temperature for 30 min and then concentrate the reaction mixture. Purify the resulting residue by flash silica gel chromatography (0-50% EtOAc in hexanes, then switch to 3% MeOH in CH2Cl2) to yield a solid. Dissolve the solid in MeOH (1 mL) and treat with 1 N aqueous HCl (0.13 mL, 0.13 mmol). Concentrate the solution to obtain the title compound as a solid (0.065 g, 29%). ES/MS m/z 476.0 (M+1).

Workup

  1. customthe reaction at ambient temperature for 30 min
  2. concentrationconcentrate the reaction mixture
  3. customPurify the resulting residue by flash silica gel chromatography (0-50% EtOAc in hexanes
  4. customto yield a solid
  5. concentrationConcentrate the solution

Sources & evidence

ORD record
ord-8fd715f719b841aa837b6f85fb5ca3b3
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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