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Hydrochloric Acid → 6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid

HRID 42209
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 592406356-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536168B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes