Dichloromethane → HCID 10192976, compound
Reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:12][N:13](C(OCC3C=CC=CC=3)=O)[CH2:14][CH2:15][N:7]3[C:8]=2[C:3]=1[CH:4]1[CH2:28][CH2:27][CH2:26][CH:5]1[CH2:6]3.FC(F)(F)S(O)(=O)=O.C1(OC)C=CC=CC=1.[OH-].[Na+].C(Cl)[Cl:48]>>[ClH:48].[F:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:12][NH:13][CH2:14][CH2:15][N:7]3[C:8]=2[C:3]=1[CH:4]1[CH2:28][CH2:27][CH2:26][CH:5]1[CH2:6]3Participants
Procedure
The compound of Example 25 (0.350 g, 0.92 mmol) was dissolved in methylene chloride (1.41 mL). Trifluoromethane sulfonic acid (0.570 mL, 6.4 mmol) and anisole (0.300 mL, 2.7 mmol) were added at room temperature. After 4.5 hours, the pH of the reaction mixture was adjusted to a pH of 8 to 9 with 1N NaOH, and the solution was stirred for 20 minutes. The contents of the flask were transferred to a separatory funnel and extracted with methylene chloride (3×). The combined organic extracts were dried with magnesium sulfate, filtered and concentrated. Further purification (15% ammonia in 2M solution ethanol/ethyl acetate) gave 0.1514 g of the desired free amine product as a yellow oil (67%). The free amine product (0.1514 g, 0.61 mmol) was dissolved in diethyl ether, and then HCl in 2M solution of diethyl ether was added. The mixture was stirred for 30 minutes and a pale yellow solid was filtered off.
Workup
- customThe contents of the flask were transferred to a separatory funnel
- extractionextracted with methylene chloride (3×)
- dry with materialThe combined organic extracts were dried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customFurther purification (15% ammonia in 2M solution ethanol/ethyl acetate)
Sources & evidence
- ORD record
- ord-b84785170892480a9080b9fffcb0f883
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687620B2
Reaction notes
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