1-Methylimidazole → HCID 57340965, compound
Reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.CN1C=CN=C1.[F:18][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=O.[NH2:28][C:29]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[C:34]([CH2:40][CH3:41])[C:30]=1[C:31](O)=[O:32]>C(Cl)Cl>[CH2:40]([C:34]1[C:30]2[C:31](=[O:32])[O:23][C:21]([C:20]3[C:19]([F:18])=[N:27][CH:26]=[CH:25][CH:24]=3)=[N:28][C:29]=2[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=1)[CH3:41]Participants
Conditions
- Temperature
- 0 °C
Procedure
TsCl (275 mg, 1.44 mmol) and N-methylimidazole (285 uL, 3.60 mmol) were added at 0° C. to a suspension of 2-fluoro-nicotinic acid (169 mg, 1.20 mmol) in CH2Cl2 (3 mL) under Ar atmosphere. The mixture was stirred at 0° C. for 1 hour. Compound R (195 mg, 1.00 mmol) was added to the mixture at 0° C. over 5 minutes and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. N-methylimidazole (47.5 uL, 0.60 mmol) and TsCl (114 mg, 0.60 mmol) were added at 0° C. to the mixture, and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was washed with saturated NaHCO3 (aq.), water (5 times) and brine. The organic phase was then dried over anhydrous Na2SO4 and concentrated in vacuo to afford compound S (300 mg, 1.00 mmol) as a white powder.
Workup
- stirringthe mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour
- stirringthe mixture was stirred at 0° C. for 1 hour
- extractionextracted with EtOAc
- washThe organic layer was washed with saturated NaHCO3 (aq.), water (5 times) and brine
- dry with materialThe organic phase was then dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-030ccb04820d4b9aa6a58dc1bdfe721d
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879846B2
Reaction notes
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