Triethylamine → HCID 178499408, compound
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1)=O.Cl.Cl.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([C:30]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:31])[CH2:25]2)=[N:21][C:22]=1[NH2:23].S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].C(N(CC)CC)C>O.C(O)C>[N:32]1([C:30]([C@@H:26]2[CH2:27][CH2:28][CH2:29][N:24]([C:20]3[N:21]=[C:22]4[NH:23][C:1]([C:3]5[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=5)=[N:16][C:17]4=[CH:18][CH:19]=3)[CH2:25]2)=[O:31])[CH2:36][CH2:35][CH2:34][CH2:33]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
Into a vial was added methyl 2-(3-formylphenyl)acetate (98 mg, 0.55 mmol), (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Intermediate 1, Step 3) (140 mg, 0.45 mmol) and ethanol (1.5 mL). Then sodium dithionate (388 mg, 2.23 mmol) and water (0.5 mL) were added to the mixture. The vial was sealed. The reaction mixture was heated to 110° C. for 18 h. The solution was cooled to room temperature. Triethylamine (0.15 mL, 1.1 mmol) was added and the solution was stirred at 100° C. for 18 h. A sample (0.8 mL) of the solution was removed and concentrated to dryness, and the resulting residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 448.2; HPLC retention time 2.28 min (Method A).
Workup
- customThe vial was sealed
- temperatureThe solution was cooled to room temperature
- customA sample (0.8 mL) of the solution was removed
- concentrationconcentrated to dryness
- customthe resulting residue was purified via HPLC
Sources & evidence
- ORD record
- ord-3f9a2534368a4eb3b118866f79b374cd
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296745B2
Reaction notes
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