Diethylamine → N-[5-(2-aminophenyl)pent-4-ynyl]-2-(S)-(2,2,2-trifluoroacetylamino)butyramide

HRID 1039020Notes

Reaction equation

HRID 1039020 reaction equation
[CH2:1]([NH:6][C:7](=[O:18])[C@@H:8]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][CH3:10])[CH2:2][CH2:3][C:4]#[CH:5].I[C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].C(NCC)C>[Cu](I)I>[NH2:22][C:21]1[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=1[C:5]#[C:4][CH2:3][CH2:2][CH2:1][NH:6][C:7](=[O:18])[C@@H:8]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 119952-IodoanilineHCID 86653105(S)-N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide

Product 1

HCID 86654753N-[5-(2-aminophenyl)pent-4-ynyl]-2-(S)-(2,2,2-trifluoroacetylamino)butyramide

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

A 50 mL round bottom flask was charged with (S)—N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide (110 mg, 0.42 mmol), 2-iodoaniline (89.0 mg, 0.41 mmol), copper iodide (13.0 mg, 0.068 mmol), palladium tetrakistriphenylphosphine (47 mg, 0.041 mmol), and diethylamine (12.6 mL). The resulting mixture was stirred at room temperature for 4 h, concentrated in vacuo and the resulting residue purified via flash silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 90:10-10:90 Heptane:EtOAc) to yield N-[5-(2-aminophenyl)pent-4-ynyl]-2-(S)-(2,2,2-trifluoroacetylamino)butyramide. 1H NMR (300 MHz, CDCl3) δ 7.21-7.24 (m, 1H), 7.07-7.12 (m, 1H), 6.64-6.71 (m, 1H), 6.42-6.46 (m, 1H), 4.38-4.45 (m, 1H), 3.39-3.53 (m, 2H), 2.53 (t, J=6.8 Hz, 2H), 1.67-1.96 (m, 4H), and 0.88-0.93 (m, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe resulting residue purified via flash silica gel chromatography (Analogix IF-280

Sources & evidence

ORD record
ord-2726fd22312a40428c4fbd80c8b4f8e5
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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