Sodium Bicarbonate → HCID 11666897, compound
Reaction equation
Cl.[CH3:2][N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:6]=2[C:5]([CH3:21])=[C:4]1[CH3:22].C(=O)(O)[O-].[Na+]>>[CH3:2][N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:6]=2[C:5]([CH3:21])=[C:4]1[CH3:22]Participants
Procedure
The compound (20 mg, 0.061 mmol) prepared in Example 34 was treated with a saturated sodium bicarbonate solution to obtain 1,2,3-trimethyl-4-(4-fluorobenzylamino)-1H-pyrrolo[3,2-c]pyridine (17 mg, 0.060 mmol). Triethylamine (0.013 ml, 0.090 mmol) and acetyl chloride (0.006 ml, 0.090 mmol) were added to a solution of 1,2,3-trimethyl-4-(4-fluorobenzylamino)-1H-pyrrolo[3,2-c]pyridine (17 mg, 0.060 mmol) in tetrahydrofuran (2 nit). The reaction mixture was stirred for 30 minutes at room temperature and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate), dissolved in ethyl acetate (1 ml), and then saturated with hydrochloric acid gas. The resulting precipitate was filtered to give the titled compound as a white solid. (Yield: 80.5%).
Sources & evidence
- ORD record
- ord-ca9f2469ef8441dbaa91aaa52d4915f8
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513277B2
Reaction notes
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