Pyridine → HCID 59300689, compound

HRID 1675281Notes

Reaction equation

HRID 1675281 reaction equation
[OH:1][N:2]=[CH:3][C@H:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[CH:19]=2)=[CH:12][CH:11]=1)[CH2:5][C:6]([O:8][CH3:9])=[O:7].N1C=C[CH:37]=[CH:36][CH:35]=1.C1C(=O)N(Cl)C(=O)C1.CC#C>C(Cl)Cl>[F:33][C:30]([F:32])([F:31])[C:27]1[CH:26]=[CH:25][C:24]([C:20]2[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=2)[CH2:17][O:16][C:13]2[CH:12]=[CH:11][C:10]([C@@H:4]([C:3]3[CH:35]=[C:36]([CH3:37])[O:1][N:2]=3)[CH2:5][C:6]([O:8][CH3:9])=[O:7])=[CH:15][CH:14]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6335PropyneHCID 31398Chlorosuccinimide2×HCID 86619684Methyl (βS)-β-[(hydroxyimino)methyl]-4-[[4′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]methoxy]benzenepropanoate

Product 1

HCID 59300689HCID 59300689, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 39.2 (100 mg, 0.22 mmol) was dissolved in DCM, and pyridine (0.05 mL) and NCS (30 mg, 0.22 mmol) were added. The resulting mixture was stirred at room temperature for 3 hours. Additional NCS (60 mg) was added, and the mixture was left at room temperature overnight. Then TEA (0.4 mL) was added to the mixture, and a stream of methylacetylene was passed through the reaction mixture for 20 minutes. LCMS detected the desired product. The solvent was removed, and the residue was purified by CombiFlash to give 39.3.

Workup

  1. waitthe mixture was left at room temperature overnight

Sources & evidence

ORD record
ord-224d7ccf449046abb6b656cc86e09301
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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