Triethylamine → 4-[(Cyclopropylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)-benzamide

HRID 2217925Notes

Reaction equation

HRID 2217925 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].[CH:24]1([CH2:27][NH2:28])[CH2:26][CH2:25]1.CCN(CC)CC>CCO>[CH:24]1([CH2:27][NH:28][C:2]2[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:9][C:10]([F:12])([F:11])[F:13])[CH2:14][C:15]([F:18])([F:16])[F:17])=[O:7])=[CH:4][C:3]=2[N+:21]([O-:23])=[O:22])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75646CyclopropanemethanamineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 588744874-[(Cyclopropylmethyl)amino]-3-nitro-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 (100 mg, 0.287 mmol) and cyclopropylmethyl amine (0.030 mL, 0.344 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: 91 mg (80%); 1H NMR (CDCl3) 0.35 (m, 2H), 0.70 (m, 2H), 1.21 (m, 1H), 3.21 (m, 2H), 4.25 (q, J=8.59 Hz, 4H), 6.91 (d, J=8.98 Hz, 1H), 7.54 (d, J=8.79 Hz, 1H), 8.30 (s, 1H), 8.35 (s, 1H); MS (ESI) 400.19 (MH+).

Workup

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

Sources & evidence

ORD record
ord-59971d8bf0704e50b7b89a2c1d5a992a
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

Loading…