Dimethylamine → HCID 25124728, compound

HRID 1929785Notes

Reaction equation

HRID 1929785 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=2[O:23][CH3:24])[N:19]=[CH:18][N:17]=[C:16]3[NH:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([Cl:33])[C:27]=2[F:34])[CH2:8]1)=[O:6].[CH3:35][NH:36][CH3:37].C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:33][C:28]1[C:27]([F:34])=[C:26]([NH:25][C:16]2[C:15]3[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:13]([O:12][C@H:9]4[CH2:10][CH2:11][N:7]([C:5](=[O:6])/[CH:4]=[CH:3]/[CH2:2][N:36]([CH3:37])[CH3:35])[CH2:8]4)[CH:14]=3)[N:19]=[CH:18][N:17]=2)[CH:31]=[CH:30][C:29]=1[F:32]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 68748519HCID 68748519, compound

Product 1

HCID 25124728HCID 25124728, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

580 mg of the compound obtained in step 1) was dissolved in 10 ml of tetrahydrofuran at 0° C., and 5 ml of a 1.0 M dimethylamine-containing tetrahydrofuran solution was added thereto. The resulting mixture was stirred at room temperature for one hour, a saturated sodium bicarbonate was added thereto, and the resulting solution was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was purified by column chromatography (chloroform:methanol=30:1) to obtain the title compound (175 mg, 32%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationdistilled under a reduced pressure
  6. customThe resulting residue was purified by column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-207c3d84262645ec9ae2e214e63b4918
Source dataset
uspto-grants-2012_05
Patent number
US08188102B2

Reaction notes

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