4-Methylmorpholine → HCID 59679993, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]2[S:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[N:21]=2)[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]2[S:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[N:21]=2)[CH:12]=1)([O-:3])=[O:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
3-Nitro-5-thiazolo[5,4-c]pyridin-2-yl-benzoic acid (880 mg, 2.92 mmol) was suspended in 50 mL of anhydrous THF along with NMM (0.32 mL, 2.92 mmol). The reaction mixture was cooled in an ice bath and isobutyl chloroformate (0.38 mL, 2.92 mmol) was added. The reaction mixture was stirred at 0° C. for 40 min. NaBH4 (110 mg, 2.92 mmol) was then added as a solution in 5 mL of water. The reaction mixture was stirred at 0° C. for 30 min and then warmed to room temperature. It was concentrated and then extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated to afford the crude product. Purification by chromatography (Isco, gradient elution, CH2Cl2 to 9:1 CH2Cl2/MeOH) afford 150 mg of (3-nitro-5-thiazolo[5,4-c]pyridin-2-yl-phenyl)-methanol.
Workup
- temperatureThe reaction mixture was cooled in an ice bath
- stirringThe reaction mixture was stirred at 0° C. for 30 min
- temperaturewarmed to room temperature
- concentrationIt was concentrated
- extractionextracted with CH2Cl2
- dry with materialThe combined organic layers were dried (Na2SO4)
- concentrationconcentrated
- customto afford the crude product
- customPurification
- washby chromatography (Isco, gradient elution, CH2Cl2 to 9:1 CH2Cl2/MeOH)
Sources & evidence
- ORD record
- ord-4d554ebe1c9b4e798f6bba03c5a32c6e
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345178B2
Reaction notes
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