Diisopropylethylamine → HCID 86590192, compound

HRID 1829992Notes

Reaction equation

HRID 1829992 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]2[C:13]([OH:15])=[O:14])[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O[C:30]1[C:35]([F:36])=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40])=O>CN(C=O)C>[F:36][C:35]1[C:30]([O:14][C:13]([C:6]2[N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=2)=[O:15])=[C:31]([F:40])[C:32]([F:39])=[C:33]([F:38])[C:34]=1[F:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 10921744HCID 10921744, compound

Product 1

HCID 86590192HCID 86590192, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-cyclopropylmethyl-4-nitro-1H-pyrrole-2-carboxylic acid (8.07 g, 38.39 mmol) in anhydrous DMF (120 ml) in the presence of N,N-diisopropylethyl-amine (7.69 ml) was added dropwise pentafluorophenyl trifluoroacetate (7.59 ml, 44.15 mmol) at 0° C. The reaction mixture was then stirred at room temperature for 5 h. After removal of solvent, the crude product was purified by chromatography on silica gel eluted by toluene-ethyl acetate (50:1) to give compound 278 (14.28 g, 98%) as a white powder. H1-NMR (DMSO-d6) 8.58 (d, 1H), 7.84 (d, 1H), 4.22 (d, 2H), 1.32−1.06 (m, 1H), 0.55–0.51 (m, 2H), 0.45−0.42 (m, 2H).

Workup

  1. customAfter removal of solvent
  2. customthe crude product was purified by chromatography on silica gel
  3. washeluted by toluene-ethyl acetate (50:1)

Sources & evidence

ORD record
ord-0e2792a9c8864c92aea69612b84ffd58
Source dataset
uspto-grants-2006_06
Patent number
US07064218B2

Reaction notes

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