Thionyl Chloride → HCID 10366592, compound

HRID 971134Notes

Reaction equation

HRID 971134 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:30])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([C:27]([NH2:29])=O)[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:31]([F:34])([F:33])[F:32])=[N:10]2)=[CH:5][CH:4]=1.O=S(Cl)Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:30])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([C:27]#[N:29])[CH2:25][CH2:26]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:31]([F:34])([F:32])[F:33])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10073425HCID 10073425, compound

Product 1

HCID 10366592HCID 10366592, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 14 (22 mg, 0.047 mmol) was stirred in DMF (0.3 mL) at RT in a capped vial. SOCl2 (0.05 mL) was added. The mixture was stirred at RT for 1.5 h. LC-MS showed completion of the reaction. Prep LC-MS purification (35–98% CH3CN in H2O) provided the title compound (15 mg, yield, 71%). LC/MS(ESI+) 453.4 (M+H)+, tR=5.24 min. 1H NMR (acetone-d6) δ 7.50 (d, J=9.2 Hz, 2H), 7.39 (m, 4H), 6.97 (d, J=8.8 Hz, 2H), 4.18 (t, J=6.6 Hz, 2H), 3.84 (s, 3H), 3.17 (t, J=6.6 Hz, 2H), 1.71 (m, 2H), 1.48 (m, 2H) ppm. 19F NMR (acetone-d6) δ −77.16 ppm.

Workup

  1. customcompletion of the reaction
  2. customPrep LC-MS purification (35–98% CH3CN in H2O)

Sources & evidence

ORD record
ord-0bc2c9ae9e4841279f603281ccf0c8bd
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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