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Thionyl Chloride → HCID 68352149, compound

HRID 2174552
Notes
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Reaction equation

HRID 2174552 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([CH2:10][C:11]([OH:13])=O)[CH:9]=1)=[O:4].S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[C:22]([C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)=[CH:21][C:20]=1[C:38]([O:40][CH3:41])=[O:39]>C1(C)C=CC=CC=1.ClCCl>[Cl:25][C:23]1[CH:24]=[C:19]([NH:18][C:11](=[O:13])[CH2:10][N:8]2[CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[N:7]2)[C:20]([C:38]([O:40][CH3:41])=[O:39])=[CH:21][C:22]=1[C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:30][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 19576734[4-(methoxycarbonyl)-1H-pyrazol-1-yl]acetic acidHCID 68352047HCID 68352047, compound2×

Product 1

HCID 68352149HCID 68352149, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(4-(methoxycarbonyl)-1H-pyrazol-1-yl)acetic acid (ChemCollect GmbH, 401 mg, 2.175 mmol) in toluene (10 mL) was added thionyl chloride (0.317 mL, 4.35 mmol) and the reaction mixture was stirred at 90° C. for 2 h. The solvent was removed under reduced pressure and the residue was added to a solution of methyl 4-amino-6-chloro-4′-(piperidin-1-yl)-[1,1′-biphenyl]-3-carboxylate (Intermediate 48) (500 mg, 1.45 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature overnight. Solvent was removed under reduced pressure and water was added. Precipitate was observed, solid was filtered and dried to give the title compound methyl 1-(2-((2-chloro-5-(methoxycarbonyl)-4′-(piperidin-1-yl)-[1,1′-biphenyl]-4-yl)amino)-2-oxoethyl)-1H-pyrazole-4-carboxylate (720 mg, 1.409 mmol, 97% yield) as a cream solid. LCMS: (M+H)+=511; Rt=4.04 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customSolvent was removed under reduced pressure and water
  4. additionwas added
  5. filtrationsolid was filtered
  6. customdried

Sources & evidence

ORD record
ord-273341e8e9454b4a842a380b9b47784c
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09061998B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes