Thionyl Chloride → HCID 89622618, compound

HRID 1500814Notes

Reaction equation

HRID 1500814 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]CN(C(C)C)C(C)C>ClCCl.CO>[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][CH3:31])=[C:10]([C:11]#[N:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 89622234HCID 89622234, compound

Product 1

HCID 89622618HCID 89622618, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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 methanol (2 ml) and treated with DIPEA (57 μl, 328 μmol). The mixture was stirred first 2 h at 60° C., then refluxed overnight and finally 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 methanol and filtered through an anion exchange cartridge (Stratospheres SPE, PL-HCO3 MP-resin). The cartridge was eluted with methanol, and the filtrate was evaporated affording 18 mg (28% of th.) of the title compound.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in methanol (2 ml)
  3. stirringThe mixture was stirred first 2 h at 60° C.
  4. temperaturerefluxed overnight
  5. temperaturefinally heated to 150° C. for 30 min in a microwave device
  6. customAfter this, the mixture was evaporated
  7. customthe residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. TFA)
  8. customThe product thus obtained
  9. filtrationfiltered through an anion exchange cartridge (Stratospheres SPE, PL-HCO3 MP-resin)
  10. washThe cartridge was eluted with methanol
  11. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b95e104ef9e245d6873ae4004c6e98eb
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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