Dimethylamine, hydrochloride → HCID 69589133, compound

HRID 1245013Notes

Reaction equation

HRID 1245013 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=O)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl.[CH3:24][NH:25][CH3:26].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.O1CCCC1>[CH3:24][N:25]([CH3:26])[CH2:21][CH:20]=[CH:19][C:11]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[NH:9][CH:10]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 73853384HCID 73853384, compound

Product 1

HCID 69589133HCID 69589133, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

700 mg (2.38 mmol) of 3-[2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrol-4-yl]acrylaldehyde [prepared as described in step 66 (i) above] and 1.95 g (23.8 mmol) of dimethylamine hydrochloride were dissolved in 110 ml of a 1:1 by volume mixture of methanol and tetrahydrofuran, after which 226 mg (3.59 mmol) of sodium cyanotrihydridoborate were added to the solution. The resulting mixture was stirred at room temperature for 19 hours. At the end of this time, the reaction mixture was added to a saturated aqueous solution of sodium hydrogencarbonate and then this was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 20:1:1 by volume mixture of ethyl acetate, methanol and isopropylamine as the eluant to give 429 mg (yield 56%) of the title compound as a white powder.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by chromatography on a silica gel column
  8. additionby volume mixture of ethyl acetate, methanol and isopropylamine as the eluant

Sources & evidence

ORD record
ord-328c7fc33a124ed9a7b3eef45308d087
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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