Dimethyl Sulfoxide → HCID 25014406, compound

HRID 421744Notes

Reaction equation

HRID 421744 reaction equation
C[N:2]([C:29]1[CH:34]=CC=CC=1)[S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:26]=[CH:25][C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)[CH:18]=[C:13]3[C:12](=[O:27])[C:11]=2[CH:28]=1)(=[O:5])=[O:4].C[N:36]1CC[CH2:38][C:37]1=O.C(N(CC)CC)C.C[S:50](C)=O>O>[CH3:24][N:22]1[CH:23]=[C:19]([C:17]2[CH:18]=[C:13]3[C:12](=[O:27])[C:11]4[CH:28]=[C:7]([CH2:6][S:3]([NH:2][CH2:29][C:34]5[S:50][CH:38]=[CH:37][N:36]=5)(=[O:5])=[O:4])[CH:8]=[CH:9][C:10]=4[CH:26]=[CH:25][C:14]3=[N:15][CH:16]=2)[CH:20]=[N:21]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471Triethylamine3×HCID 13387N-methyl-2-pyrrolidoneHCID 25014404HCID 25014404, compound2×

Product 1

HCID 25014406HCID 25014406, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

Compounds in Table 2 were prepared in analogy to the procedures described for the preparation of Compounds 5-6 and 6-1 as follows: Either Compound 5-4 (1.0 equivalents) or Compound 7-1 (1.0 equivalents) and either an amine (1.0 to 5.0 equivalents) or an amine salt (1.0 to 5.0 equivalents) were combined in a vial with enough N-methyl-2-pyrrolidinone to generate a 0.1M solution of either Compound 5-4 or Compound 7-1. Triethylamine (1:1 molar ratio to the amine salt) was then added to reactions utilizing amine salts composed of a 1:1 ratio of amine to acid. Triethylamine (2:1 molar ratio to the amine salt) was then added to reactions utilizing amine salts composed of a 1:2 ratio of amine to acid. No triethylamine was added when amine freebases were employed. The vial was then sealed and the resulting solution or suspension was heated and stirred at 180° C. with conventional heating. After the reaction was judged to be complete by LCMS analysis, the reaction was cooled to room temperature and diluted in DMSO and water. The resulting solution was filtered and purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford the title compounds.

Workup

  1. customCompounds in Table 2 were prepared in analogy to the procedures
  2. customThe vial was then sealed
  3. temperaturethe resulting solution or suspension was heated
  4. temperaturethe reaction was cooled to room temperature
  5. filtrationThe resulting solution was filtered
  6. custompurified by preparative HPLC Reverse phase (C-18)
  7. washeluting with Acetonitrile/Water+0.05% TFA

Sources & evidence

ORD record
ord-fc361bc2ae984f789882df8cb70109b3
Source dataset
uspto-grants-2012_01
Patent number
US08101603B2

Reaction notes

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