Triethylamine → HCID 58874491, compound

HRID 2217934Notes

Reaction equation

HRID 2217934 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].CC[N:26]([CH2:29][CH3:30])CC>CCO>[N+:21]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:2]=1[NH:26][CH2:29][CH:30]1[CH2:3][CH2:4][CH2:5][CH2:6][O:7]1)[C:6]([N:8]([CH2:14][C:15]([F:18])([F:16])[F:17])[CH2:9][C:10]([F:13])([F:11])[F:12])=[O:7])([O-:23])=[O:22]

Participants

4

Reactant 2

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

Product 1

HCID 58874491HCID 58874491, compound

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 (83 mg, 0.238 mmol) and R/S-2-aminomethyl-tetrahydropyran hydrochloride (40 mg, 0.262 mmol) in 3 mL of EtOH containing Et3N (0.070 mL, 0.476 mmol). The product was purified by flash chromatography on silica gel using 2:1/hexanes:EtOAc as eluent. Yield: 100 mg (95%); 1H NMR (CDCl3) 1.48 (m, 1H), 1.58 (m, 3H), 1.68 (m, 1H), 1.95 (m, 1H), 3.35 (m, 1H), 3.41 (m, 1H), 3.52 (m, 1H), 3.64 (m, 1H), 4.07 (m, 1H), 4.26 (m, 4H), 6.96 (d, J=8.98 Hz, 1H), 7.54 (d, J=8.98 Hz, 1H), 8.31 (s, 1H), 8.55 (brs, 1H); MS (ESI) 530.21 (MH+).

Workup

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

Sources & evidence

ORD record
ord-d76f528a838f4f20ad5d3bfc1b1c818d
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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