Thionyl Chloride → HCID 86639153, compound

HRID 1666912Notes

Reaction equation

HRID 1666912 reaction equation
S(Cl)(Cl)=O.[CH2:5]([N:7]1[C:11]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:25]4[C:26]([CH3:30])=[C:27]([CH3:29])[S:28][C:24]=4[N:23]4[C:31]([CH3:34])=[N:32][N:33]=[C:22]4[C@H:21]([CH2:35][C:36]([OH:38])=[O:37])[N:20]=3)=[CH:15][CH:14]=2)=[CH:10][CH:9]=[N:8]1)[CH3:6].[CH3:39][O:40][CH:41](O)[CH3:42]>>[CH2:5]([N:7]1[C:11]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:25]4[C:26]([CH3:30])=[C:27]([CH3:29])[S:28][C:24]=4[N:23]4[C:31]([CH3:34])=[N:32][N:33]=[C:22]4[C@H:21]([CH2:35][C:36]([O:38][CH2:42][CH2:41][O:40][CH3:39])=[O:37])[N:20]=3)=[CH:17][CH:18]=2)=[CH:10][CH:9]=[N:8]1)[CH3:6]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 30156371-MethoxyethanolHCID 67445342HCID 67445342, compound

Product 1

HCID 86639153HCID 86639153, compound

Procedure

Thionyl chloride (230 μL) and the intermediate synthesized in Example 151, (S)-4-[4-(2-ethyl-2H-pyrazol-3-ylamino)phenyl]-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-acetic acid (500 mg), were successively added to methoxy ethanol (10 mL) at 0° C., and the mixture was stirred at room temperature for 1 day. After completion of the reaction, the mixture was partitioned by adding water and ethyl acetate. The organic layer was washed with aqueous sodium hydrogencarbonate, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol=100:1) to give the title compound (410 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was partitioned
  3. additionby adding water and ethyl acetate
  4. washThe organic layer was washed with aqueous sodium hydrogencarbonate
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-68f8de018ad84dd59e188034d59585c7
Source dataset
uspto-grants-2011_10
Patent number
US08044042B2

Reaction notes

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