Dichloromethane → HCID 10308809, compound

HRID 1246954Notes

Reaction equation

HRID 1246954 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14]4=[C:15]([CH2:17][N:18](C(OCC5C=CC=CC=5)=O)[CH2:19][CH2:20][N:13]4[CH2:12][CH:11]4[CH2:31][CH2:32][CH2:33][CH:10]34)[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O)(=O)=O.C1(OC)C=CC=CC=1.[OH-].[Na+].C(Cl)[Cl:53]>O>[ClH:53].[C:1]1([C:7]2[CH:8]=[C:9]3[C:14]4=[C:15]([CH2:17][NH:18][CH2:19][CH2:20][N:13]4[CH2:12][CH:11]4[CH2:31][CH2:32][CH2:33][CH:10]34)[CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 6344Dichloromethane2×HCID 7519AnisoleHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 10216779HCID 10216779, compound2×

Product 1

HCID 10308809HCID 10308809, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound of example 21 (0.255 g, 0.581 mmol) was dissolved in methylene chloride (0.89 mL). To the solution of Example 21 was added trifluoromethane sulfonic acid (0.360 mL, 11.3 mmol) and anisole (0.190 mL, 1.74 mmol) at room temperature. After 45 minutes, the pH of the reaction mixture was adjusted to a pH of 9 to 10 with 1N NaOH, and then methylene chloride and water were added to the reaction flask. The contents of the flask were then transferred to a separatory funnel and extracted with methylene chloride (4×). The combined organic extracts were then dried with magnesium sulfate, filtered and concentrated. Further purification (10% ammonia in 2M solution of ethanol/ethyl acetate) yielded 0.157 g of the free amine product with some baseline impurities (80%). To purify further, the free amine was dissolved in diethyl ether/isopropanol, and then HCl in 2M solution of diethyl ether (1 eq) was added. After 30 minutes, the resulting precipitate was filtered to give the desired product.

Workup

  1. customThe contents of the flask were then transferred to a separatory funnel
  2. extractionextracted with methylene chloride (4×)
  3. dry with materialThe combined organic extracts were then dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customFurther purification (10% ammonia in 2M solution of ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-820a071b6a464143b4496beaf9854a3d
Source dataset
uspto-grants-2006_10
Patent number
US07129237B2

Reaction notes

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