Hydrochloric Acid → HCID 59240635, compound

HRID 42209Notes

Reaction equation

HRID 42209 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)=[N:19][N:18]=3)[CH2:13][CH2:12]2)=[N:7][CH:6]=1)C.[OH-].[Li+].C1COCC1.Cl>O.CO>[F:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]([N:14]3[CH2:13][CH2:12][N:11]([C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:35])=[O:3])=[CH:6][N:7]=4)[CH2:16][CH2:15]3)=[N:18][N:19]=2)=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 592406536-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid ethyl ester

Product 1

HCID 59240635HCID 59240635, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid ethyl ester (188 mg, 0.4 mmol), Lithium hydroxide (96 mg, 4.0 mmol), THF (750 μL), MeOH (750 μL), and H2O (400 μL) are combined at room temperature and stirred 16 h. Adjust pH to between three and four with 1N HCl. Extract with CH2Cl2/EtOH 4:1 and combined organics are washed with brine. Concentrate in vacuo to yield the title compound without further purification (165 mg, 93%).

Workup

  1. customare combined at room temperature
  2. extractionExtract with CH2Cl2/EtOH 4:1
  3. washcombined organics are washed with brine
  4. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-79c2c2eb29594df8b78e6394d8a9e248
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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