Water → HCID 178497690, compound
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[NH2:13][C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])[CH2:21]2)[CH:17]=[CH:16][C:15]=1[N+:33]([O-])=O.S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].O>C(O)C.C(N(CC)CC)C>[N:28]1([C:26]([C@@H:22]2[CH2:23][CH2:24][CH2:25][N:20]([C:18]3[N:19]=[C:14]4[NH:13][C:1]([C:3]5[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=5)[C:6]([O:8][CH3:9])=[O:7])=[N:33][C:15]4=[CH:16][CH:17]=3)[CH2:21]2)=[O:27])[CH2:32][CH2:31][CH2:30][CH2:29]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
Into a vial was added methyl 3-formylbenzoate (102 mg, 0.6 mmol) and a solution of (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (140 mg, 0.4 mmol) in ethanol (1.5 mL). Sodium dithionate (388 mg, 2.2 mmol) and water (0.5 mL) were added. The vial was sealed and the solution was stirred 110° C. for 18 h. The solution was cooled to room temperature and triethylamine (0.1 mL) was added. The solution was stirred at 100° C. for 18 h. An aliquot of 0.8 mL was removed and concentrated to dryness, and the resulting residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 434.2; HPLC retention time 2.25 min (Method A).
Workup
- customThe vial was sealed
- temperatureThe solution was cooled to room temperature
- stirringThe solution was stirred at 100° C. for 18 h
- customAn aliquot of 0.8 mL was removed
- concentrationconcentrated to dryness
- customthe resulting residue was purified via HPLC
Sources & evidence
- ORD record
- ord-c3f2969c1f154a428223e4f5ee6b2ca8
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296745B2
Reaction notes
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