HCID 16658949, compound → HCID 16659514, compound

HRID 990957Notes

Reaction equation

HRID 990957 reaction equation
[CH:1]([C@H:4]1[N:9]([CH2:10][C:11]([F:14])([F:13])[F:12])[C:8]2[CH:15]=[CH:16][C:17]([N+:19]([O-])=O)=[CH:18][C:7]=2[O:6][CH2:5]1)([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[NH2:19][C:17]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:10][C:11]([F:14])([F:13])[F:12])[C@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][O:6][C:7]=2[CH:18]=1

Participants

4

Reactant 1

HCID 16658949HCID 16658949, compound

Product 1

HCID 16659514HCID 16659514, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared according to General Method 4 (EXAMPLE 1) from (3R)-3,4-dihydro-3-isopropyl-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine (0.350 g, 1.15 mmol) and 10% Pd/C (0.14 g) in 7 mL EtOAc to afford 0.284 g (90%) of (3R)-7-amino-3,4-dihydro-3-isopropyl-4-(2,2,2-trifluoroethyl)-2H-1,4benzoxazine after purification by flash chromatography (gradient elution, hexanes:EtOAc 9:1 to 3:1). Data for (3R)-7-amino-3,4-dihydro-3-isopropyl-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine: Rf 0.2 (3:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 6.71 (d, 1H, J=8.5), 6.27 (dd, 1H, J=8.5, 2.6), 6.20 (d, 1H, J=2.5), 4.34 (dd, 1H, ABX, J=11.0, 1.5), 3.84 (dd, 1H, ABX, J=11.3, 2.2), 3.71-3.47 (m, 2H), 3.41 (broad s, 2H), 2.62 (d, 1H, J=9.8), 1.81-1.70 (m, 1H), 0.98 (d, 3H, J=6.7), 0.96 (d, 3H, J=6.7).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-dd26c5c8a7b148e9a1504ff0f729b253
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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