HCID 18416130, compound → HCID 18416175, compound

HRID 990948Notes

Reaction equation

HRID 990948 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[N:8]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH:9]([C:12]([F:15])([F:14])[F:13])[CH2:10][O:11][C:6]=2[CH:5]=1)([O-])=O>[Pd]>[NH2:1][C:4]1[CH:22]=[CH:21][C:7]2[N:8]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH:9]([C:12]([F:13])([F:14])[F:15])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

3

Reactant 1

HCID 18416130HCID 18416130, compound

Product 1

HCID 18416175HCID 18416175, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This compound was prepared by General Method 4 (EXAMPLE 1) from (+)-3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)-2H-1,4-benzoxazine (45 mg, 0.16 mmol) and 10% Pd-C (30 mg) and purified by flash chromatography (EtOAc:hexanes, 1:1) to afford 26 mg (65%) of (±)-7-amino-3,4-dihydro-4-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)-2H-1,4-benzoxazine. Data for (±)-7-amino-3,4-dihydro-4-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)-2H-1,4-benzoxazine: 1H NMR (400 MHz, CDCl3) 6.68 (d, 1H, J=8.4), 6.32-6.28 (m, 2H), 4.56 (dd, 1H, J=12.0, 0.96), 4.16-4.00 (m, 2H), 3.84-3.69 (m, 2H), 3.60-3.32 (m, 2H).

Workup

  1. custompurified by flash chromatography (EtOAc:hexanes, 1:1)

Sources & evidence

ORD record
ord-706b78d1523947beb7a4118ef96fa471
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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