Triethylamine → HCID 58874494, compound

HRID 2217933Notes

Reaction equation

HRID 2217933 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][C@@H:30]1[CH2:4][CH2:5][CH2:6][O:7]1)[C:6]([N:8]([CH2:9][C:10]([F:11])([F:13])[F:12])[CH2:14][C:15]([F:16])([F:17])[F:18])=[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 58874494HCID 58874494, 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 (78 mg, 0.224 mmol) and S-(+)-tetrahydrofurfurylamine (0.025 mL, 0.246 mmol) in 3 mL of EtOH containing Et3N (0.047 mL, 0.336 mmol). The product was purified by flash chromatography on silica gel using 1:1/hexanes:EtOAc as eluent. Yield: 95 mg (95%); 1H NMR (CDCl3) 1.72 (m, 1H), 1.99 (m, 2H), 2.13 (m, 1H), 3.99 (m, 1H), 3.53 (m, 1H), 3.85 (m, 1H), 3.97 (m, 1H), 4.25 (m, 5H), 6.99 (d, J=8.98 Hz, 1H), 7.53 (d, J=8.98 Hz, 1H), 8.30 (s, 1H), 8.51 (brs, 1H); MS (ESI) 430.28 (MH+).

Workup

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

Sources & evidence

ORD record
ord-81bd8ef3753e4a9e981db59d5dd1e3c3
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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