Methanol → HCID 58874498, compound

HRID 2217937Notes

Reaction equation

HRID 2217937 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([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25]1.CO>CCO>[CH:24]1([CH2:28][NH:29][C:2]2[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:9][C:10]([F:13])([F:12])[F:11])[CH2:14][C:15]([F:16])([F:18])[F:17])=[O:7])=[CH:4][C:3]=2[N+:21]([O-:23])=[O:22])[CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 887MethanolHCID 409746CyclobutylmethylamineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 58874498HCID 58874498, 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 (237 mg, 0.680 mmol) and cyclobutylmethyl amine (0.205 mL of a 4M/MeOH solution, 0.816 mmol) in 3 mL of EtOH containing TEA (0.140 mL, 1.02 mmol). The product was purified by flash chromatography on silica gel using 3:1/hexanes:EtOAc as eluent. Yield: 262 mg (93%); 1H NMR (400 MHz, CHLOROFORM-D) δ 1.83 (m, 2H), 1.97 (m, 1H), 2.02 (m, 1H), 2.20 (m, 2H), 2.73 (m, 1H), 3.37 (m, 2H), 4.27 (m, 4H), 6.93 (d, J=8.98 Hz, 1H), 7.53 (d, J=8.79 Hz, 1H), 8.24 (m, 1H), 8.30 (m, 1H); MS (ESI) 413.95 (MH+).

Workup

  1. customThe product was purified by flash chromatography on silica gel using 3:1/hexanes

Sources & evidence

ORD record
ord-c6cddbcef8af4e41b3db6bb0983b3ac5
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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