Dimethylformamide → HCID 72550851, compound

HRID 512562Notes

Reaction equation

HRID 512562 reaction equation
[OH:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[S:13][C:12]([NH:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)=[N:11][C:10]=2[C:25]([NH2:27])=[O:26])=[O:7])=[CH:4][CH:3]=1.[C:30]([O-:33])([O-])=O.[K+].[K+].[CH3:36]N(C=O)C>O>[OH:33][CH2:30][CH2:36][O:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[S:13][C:12]([NH:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)=[N:11][C:10]=2[C:25]([NH2:27])=[O:26])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86703392HCID 86703392, compound

Product 1

HCID 72550851HCID 72550851, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 5-(4-hydroxybenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (200 mg, 0.5 mmol) and 2-bromothanol (123 mg, 1.0 mmol) in DMF (10 mL) was added K2CO3 (136 mg, 1.0 mmol), and the mixture was stirred at 80° C. for 16 hrs. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography eluted with 3.5% MeOH in DCM to give 40 mg (18% yield) of the titled compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluted with 3.5% MeOH in DCM

Sources & evidence

ORD record
ord-53cc870ab43b4fb18b0afbc45f9024fc
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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