4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid → (4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridin-2-yl)methanol
Reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([C:25](O)=[O:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1>[CH:1]1([CH2:7][NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][OH:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
3
Procedure
To a solution of the 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid (120 mg, 0.33 mmol, 1.0 eq) in 5 mL of THF was added borane-tetrahydrofuran complex (1M, 1 mL, 1 mmol) at 0° C. The reaction mixture was stirred at that temperature for 5 hours. The reaction was quenched with 1M hydrochloric acid. The resulting mixture was extracted with ethyl acetate (2×60 mL). The combined organic layers were washed with water (10 mL), brine (10 mL), then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by silica gel column eluted with ethyl acetate and hexane to give the titled compound. MH+=354.0.
Workup
- customThe reaction was quenched with 1M hydrochloric acid
- extractionThe resulting mixture was extracted with ethyl acetate (2×60 mL)
- washThe combined organic layers were washed with water (10 mL), brine (10 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
- customto give crude product, which
- customwas purified by silica gel column
- washeluted with ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-898983447b2447cb88e200edf346982f
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173689B2
Reaction notes
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