Triethylamine → 3-Nitro-4-[[(tetrahydro-2H-pyran-4-yl)methyl]amino]-N,N-bis(2,2,2-trifluoroethyl)benzamide

HRID 2217931Notes

Reaction equation

HRID 2217931 reaction equation
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[NH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CCN(CC)CC>CCO>[N+:21]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:2]=1[NH:24][CH2:25][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:6]([N:8]([CH2:14][C:15]([F:18])([F:16])[F:17])[CH2:9][C:10]([F:12])([F:11])[F:13])=[O:7])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27732104-AminomethyltetrahydropyranHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 588744863-Nitro-4-[[(tetrahydro-2H-pyran-4-yl)methyl]amino]-N,N-bis(2,2,2-trifluoroethyl)benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the general procedure for Intermediate 2 using 4-fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (75 mg, 0.215 mmol) and 4-aminomethyltetrahydropyran (27 mg, 0.236 mmol) in 3 mL of EtOH containing Et3N (0.045 mL, 0.323 mmol). The product was purified by flash chromatography on silica gel using 2:1/hexanes:EtOAc as eluent. Yield: 87 mg (91%); 1H NMR (CDCl3) 1.47 (m, 2H), 1.75 (m, 2H), 1.98 (m, 1H), 3.27 (t, J=5.47 Hz, 2H), 3.43 (m, 2H), 4.03 (m, 2H), 4.24 (q, J=8.33 Hz, 6H), 6.93 (d, J=8.98 Hz, 1H), 7.54 (d, J=8.98 Hz, 1H), 8.30 (s, 1H), 8.40 (brs, 1H); MS (ESI) 444.31 (MH+).

Workup

  1. customThe product was purified by flash chromatography on silica gel using 2:1/hexanes

Sources & evidence

ORD record
ord-6fe5120969fa4a6e8baa20bb459836e5
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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