Sodium hydride → HCID 18416149, compound

HRID 990937Notes

Reaction equation

HRID 990937 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:16][O:15][C:14]2[C:5](=[CH:6][C:7]3[C:8]([C:21]([F:24])([F:23])[F:22])=[CH:9][C:10]([O:17][CH:18]([CH3:20])[CH3:19])=[N:11][C:12]=3[CH:13]=2)[N:4]1[CH2:25][C:26]([F:29])([F:28])[F:27].[H-].[Na+].I[CH2:33][CH2:34][CH3:35]>C1COCC1>[CH:18]([O:17][C:10]1[CH:9]=[C:8]([C:21]([F:22])([F:23])[F:24])[C:7]2[CH:6]=[C:5]3[N:4]([CH2:25][C:26]([F:28])([F:29])[F:27])[CH:3]([CH2:2][O:1][CH2:33][CH2:34][CH3:35])[CH2:16][O:15][C:14]3=[CH:13][C:12]=2[N:11]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 18416140HCID 18416140, compound

Product 1

HCID 18416149HCID 18416149, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared according to General Method 16 (EXAMPLE 30) from (±)-2,3-dihydro-2-(hydroxymethyl)-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline (EXAMPLE 28) (11 mg, 0.026 mmol), NaH (5.0 mg, 0.12 mmol) and 1-iodopropane (21 mg, 0.12 mmol) in 1.0 mL THF to afford 6 mg (50%) of (±)-2,3-dihydro-7-isopropoxy-2-(1-propoxymethyl)-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline, a yellow oil, after flash chromatography (5:1 hexanes:EtOAc). Data for (±)-2,3-dihydro-7-isopropoxy-2-(1-propoxymethyl)-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline: Rf0.57 (5:1 hexanes: EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.28 (s, 1H), 7.13 (broad s, 1H), 7.00 (s, 1H), 5.48 (hept, 1H, J=6.2), 4.44 (dd, 1H, J=10.9, 1.8), 4.17 (dd, 1H, J=11.0, 2.5), 4.00-4.20 (m, 2H), 3.71 (broad t, 1H, J=6.8), 3.54-3.64 (m, 2H), 3.40 (broad t, 2H, J=6.6), 1.52-1.62 (m, 2H), 1.38 (d, 6H, J=6.2), 0.91 (t, 3H, J=7.4).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b2b43fc0b41a44ecb68ba1f05733eafc
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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