Sodium Bicarbonate → HCID 11553043, compound
Reaction equation
Cl.[CH2:2]([C:9]1[C:13]2[C:14]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[N:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]=1[CH3:27])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>>[CH2:2]([C:9]1[C:13]2[C:14]([NH:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)=[N:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]=1[CH3:27])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
Procedure
The compound (30 mg, 0.12 mmol) prepared in Example 73 was treated with a saturated sodium bicarbonate solution to obtain 3-benzyl-2-methyl-4-(4-chlorobenzylamino)-1H-pyrrolo[3,2-c]pyridine (24 mg, 0.065 mmol). Sodium hydride (60%, 4.9 mg, 0.118 mmol) was added at room temperature to a solution of 3-benzyl-2-methyl-4-(4-chlorobenzylamino)-1H-pyrrolo[3,2-c]pyridine (24 mg, 0.065 mmol) in N,N-dimethylformamide (1 ml) and then the reaction mixture was stirred for 30 minutes. Iodomethane (0.007 ml, 0.118 mmol) was added to the reaction mixture, which was then stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml) three times. The separated organic layer was dried on anhydrous magnesium sulfate, and then concentrated. 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: 58.2%)
Sources & evidence
- ORD record
- ord-305399bd3f754d86ac3dbc93356fc588
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513277B2
Reaction notes
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