Thionyl Chloride → HCID 68352149, compound

HRID 2174552Notes

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

Participants

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

customThe solvent was removed under reduced pressure
stirringThe reaction mixture was stirred at room temperature overnight
customSolvent was removed under reduced pressure and water
additionwas added
filtrationsolid was filtered
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

Loading…