Furfurylamine → HCID 58874483, compound

HRID 2217927Notes

Reaction equation

HRID 2217927 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].[CH2:24]([NH2:30])[C:25]1[O:29][CH:28]=[CH:27][CH:26]=1.CCN(CC)CC>CCO>[O:29]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:24][NH:30][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:9][C:10]([F:11])([F:12])[F:13])[CH2:14][C:15]([F:16])([F:17])[F:18])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 3438FurfurylamineHCID 8471TriethylamineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 58874483HCID 58874483, 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 (100 mg, 0.287 mmol) and furfurylamine (0.028 mL, 0.315 mmol) in 3 mL of EtOH containing Et3N (0.080 mL, 0.574 mmol). The product was purified by flash chromatography on silica gel using 4:1/hexanes:EtOAc as eluent. Yield: 115 mg (94%); 1H NMR (CDCl3) 4.23 (q, J=8.40 Hz, 4H), 4.56 (d, J=5.66 Hz, 2H), 6.31 (d, J=3.12 Hz, 1H), 6.35 (m, 1H), 7.04 (d, J=8.98 Hz, 1H), 7.39 (s, 1H), 7.53 (d, J=8.89 Hz, 1H), 8.28 (s, 1H), 8.55 (s, 1H); MS (ESI) 426.21 (MH+).

Workup

  1. customThe product was purified by flash chromatography on silica gel using 4:1/hexanes

Sources & evidence

ORD record
ord-2d18adedae254fdaae4015dc3c46557e
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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