Sodium borohydride → HCID 21094352, compound

HRID 1350161Notes

Reaction equation

HRID 1350161 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[NH:22][CH2:21][CH2:20][O:19][C:11]3=2)[N:6]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>FC(F)(F)C(O)=O>[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[N:22]([CH2:13][C:15]([F:18])([F:17])[F:16])[CH2:21][CH2:20][O:19][C:11]3=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21094349HCID 21094349, compound

Product 1

HCID 21094352HCID 21094352, compoundYield 198.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 132 was prepared according to General Method 3 (EXAMPLE 1) from 3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (20.0 mg, 0.064 mmol) and sodium borohydride (excess of 20 mg) in 3 mL trifluoroacetic acid to afford 25 mg (ca. 100%) of 3,4-dihydro-8-isopropoxy-4-(2,2,2-trifluoroethyl)-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline, a red oil. No further purification was performed and the material was directly transformed according to General Method 4 (EXAMPLE 1) from 3,4-dihydro-8-isopropoxy-4-(2,2,2-trifluoroethyl)-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (25 mg) in 0.32 mL conc. HCl and 0.64 mL glacial acetic acid heated at 70° C. for 90 minutes to afford 11 mg (49%) of Compound 132 after purification by flash chromatography (9:1 hexanes:EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (400 MHz, acetone-d6) δ 11.05 (br s, 1H), 7.31 (d, J=9.0, 1H), 7.04 (d, J=8.8, 1H), 6.92 (s, 1H), 4.32 (t, J=4.3, 2H), 4.14 (q, J=9.5, 2H), 3.61 (t, J=4.4, 2H).

Sources & evidence

ORD record
ord-02793f1c6e3641b8aea35b2d349c40d4
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

Loading…