Dimethylformamide → HCID 89659349, compound

HRID 341327Notes

Reaction equation

HRID 341327 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[C:9](Cl)[CH:8]=2)=[N:4][CH:3]=1.ON1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.CN(CCCN=[C:33]=[N:34][CH2:35][CH3:36])C.N.[CH2:38]([OH:40])[CH3:39].[C:41](=O)(O)[O-].[Na+].C[N:47]([CH:49]=[O:50])C>C(Cl)(Cl)Cl>[CH:38]([O:40][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[S:6][C:5]([C:7]3[CH:14]=[CH:13][C:10]([CH2:11][N:34]4[CH2:33][CH:36]([C:49]([NH2:47])=[O:50])[CH2:35]4)=[CH:9][CH:8]=3)=[N:4][CH:3]=2)=[CH:22][CH:21]=1)([CH3:41])[CH3:39]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 89755522HCID 89755522, compound

Product 1

HCID 89659349HCID 89659349, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound obtained in the Example 1 (150 mg) was suspended in DMF (30 ml), and 1-hydroxybenzotriazole (74.4 mg), 1-(dimethylaminopropyl)-3-ethylcarbodiimide (106 mg), and a 2 M-ammonia/ethanol solution (0.92 ml) was added to the suspension at room temperature. After the mixture was stirred overnight, chloroform and saturated sodium bicarbonate aqueous solution were added to terminate the reaction. After the aqueous layer was extracted with chloroform twice, the combined organic layer was washed with saturated brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The resulting residue was purified on column chromatography (MeOH:CHCl3=1:10) to obtain the title compound (128 mg) as a pale yellow solid.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionAfter the aqueous layer was extracted with chloroform twice
  4. washthe combined organic layer was washed with saturated brine
  5. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified on column chromatography (MeOH:CHCl3=1:10)

Sources & evidence

ORD record
ord-ac883db475e04201962f45c4cde733cb
Source dataset
uspto-grants-2014_11
Patent number
US08895753B2

Reaction notes

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