Triethylamine → HCID 60168524, compound

HRID 1845836Notes

Reaction equation

HRID 1845836 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[O:16][CH:17]([C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[C:21]([F:26])[C:20]=1[Cl:27])[CH3:18].[CH3:28][P:29](Cl)([CH3:31])=[O:30].C(N(CC)CC)C>ClCCl>[Cl:27][C:20]1[C:21]([F:26])=[CH:22][CH:23]=[C:24]([Cl:25])[C:19]=1[CH:17]([O:16][C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][O:15][P:29]([CH3:31])([CH3:28])=[O:30])=[CH:12][CH:13]=2)[CH:4]=1)[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 517954Dimethylphosphinic chlorideHCID 58688152HCID 58688152, compound

Product 1

HCID 60168524HCID 60168524, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

a mixture of [4-[6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-3-pyridyl]phenyl]methanol (15 mg, 0.037 mmol), dimethylphosphoryl chloride (50 mg, 0.45 mmol), and triethylamine (0.5 mL) in dichloromethane (10 mL) was stirred at room temperature for 1.5 hours. The solvent was removed and the residue was purified by HPLC (water/methanol, 10˜100%) to give the title compound (2 mg, 11%). ESMS: m/z 483 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by HPLC (water/methanol, 10˜100%)

Sources & evidence

ORD record
ord-2b733e4298c34d639bb0b54e58181686
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

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