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 (30 mg, 0.069 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 (25 mg, 0.068 mmol). Sodium hydride (60%, 4.2 mg, 0.102 mmol) and benzyl bromide (0.063 ml, 0.086 mmol) were added to a solution of 1,2,3-trimethyl-4-(4-fluorobenzylamino)-1H-pyrrolo[3,2-c]pyridine (25 mg, 0.068 mmol) in N,N-dimethylformamide (2 ml) and then the reaction mixture was stirred for 12 hours at 60° C. The reaction mixture was diluted with ethyl acetate (20 ml) and washed with water (10 ml) three times. The organic layer was separated, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (1 ml), saturated with hydrochloric acid gas, and then filtered to give the titled compound as a white solid. (Yield: 83.5%).
Sources & evidence
- ORD record
- ord-20a5d75ebbd2463db15982525580cce7
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513277B2
Reaction notes
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