Thionyl Chloride → HCID 22174481, compound

HRID 1797308Notes

Reaction equation

HRID 1797308 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([OH:12])=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].S(Cl)(Cl)=O.[NH2:17][C:18]1[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])=[O:33])=[C:28]([Cl:41])[CH:27]=1.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.C(Cl)Cl>[Br:24][C:22]1[CH:21]=[CH:20][C:19]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:33])=[C:28]([Cl:41])[CH:27]=2)=[C:18]([NH:17][C:10](=[O:12])[CH2:9][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8])[CH:23]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 36704(Diethoxyphosphinyl)acetic acidHCID 81531DiisopropylethylamineHCID 9801969EO-1428

Product 1

HCID 22174481HCID 22174481, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent3×

Procedure

The reactions were conducted under an argon atmosphere using oven dried glass ware. Diethylphosphonoacetic acid (0.085 mL, 0.53 mmol) was dissolved in dry toluene (1 mL) and thionylchloride (0.044 mL, 0.61 mmol) was added. The reaction mixture was refluxed for 1 h and then concentrated in vacuo. {4-[(2-Amino-4-bromophenyl)amino]-2-chlorophenyl}(2-methylphenyl)methanone (0.28 g, 0.48 mmol)(disclosed in WO 01/05744) was dissolved in dry DCM (1 mL) and N,N-diisopropylethyl amine (0.16 mL, 0.96 mmol) was added followed by drop wise addition of the above acid chloride dissolved in dry DCM (2.5 mL). The reaction mixture was stirred at room temperature for 22 h after which it was diluted with DCM. The organic phase was washed with 10% aqueous NaHCO3, H2O and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether 3:1 as the eluent to afford the title compound as an oil.

Workup

  1. customdried glass ware
  2. temperatureThe reaction mixture was refluxed for 1 h
  3. concentrationconcentrated in vacuo
  4. washThe organic phase was washed with 10% aqueous NaHCO3, H2O and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-8b23612ff3cb4a68bdab5a7b69b9d5be
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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