Thionyl Chloride → HCID 89622571, compound

HRID 1500815Notes

Reaction equation

HRID 1500815 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[S:16][C:17]4[C:23]([O:24][CH3:25])=[CH:22][C:21]([CH3:26])=[CH:20][C:18]=4[CH:19]=3)[C:9]([CH2:13][OH:14])=[C:10]([C:11]#[N:12])[N:6]2[N:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH3:31][CH2:32]N(C(C)C)C(C)C>ClCCl.C(O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[S:16][C:17]4[C:23]([O:24][CH3:25])=[CH:22][C:21]([CH3:26])=[CH:20][C:18]=4[CH:19]=3)[C:9]([CH2:13][O:14][CH2:31][CH3:32])=[C:10]([C:11]#[N:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531Diisopropylethylamine2×HCID 89622234HCID 89622234, compound

Product 1

HCID 89622571HCID 89622571, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 68 (60 mg, 164 μmol) in dichloromethane (5 ml) was treated with thionyl chloride (18 μl, 246 μmol). The mixture was stirred at rt for 15 min and then evaporated. The residue was dissolved in ethanol (2 ml) and treated with DIPEA (57 μl, 328 μmol). The mixture was stirred at 60° C. overnight and then heated to 150° C. for 30 min in a microwave device. After this, the mixture was evaporated, and the residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. TFA). The product thus obtained was dissolved in ethanol (2 ml) and again heated to 150° C. for 30 min in the microwave oven. DIPEA (57 μl, 328 μmol) was added, and heating to 150° C. in the microwave oven was continued for further 30 min. After evaporation, the residue was purified by column chromatography on silica gel (dichloromethane/methanol 95:5) affording 16 mg (23% of th.) of the title compound.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethanol (2 ml)
  3. stirringThe mixture was stirred at 60° C. overnight
  4. temperatureheated to 150° C. for 30 min in a microwave device
  5. customAfter this, the mixture was evaporated
  6. customthe residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. TFA)
  7. customThe product thus obtained
  8. temperatureagain heated to 150° C. for 30 min in the microwave oven
  9. temperatureheating to 150° C. in the microwave oven
  10. waitwas continued for further 30 min
  11. customAfter evaporation
  12. customthe residue was purified by column chromatography on silica gel (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-902d9eb19f1d4502bf42a8f2ca442b5a
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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