Diethylamine → HCID 59596674, compound

HRID 2264815Notes

Reaction equation

HRID 2264815 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]#[CH:16])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])[CH3:3].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][NH:25][C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1.C(NCC)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:4][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]#[C:16][C:29]1[CH:28]=[CH:27][C:26]([NH:25][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[F:17])=[CH:31][CH:30]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:1])[CH3:3]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoateHCID 28878728HCID 28878728, compound

Product 1

HCID 59596674HCID 59596674, compoundYield 28.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate (D64, 365 mg, 1.60 mmol), prepared with analogous procedure to that described hereinabove, N-[(2-fluorophenyl)methyl]-4-iodoaniline (D63, 630 mg, 1.92 mmol) and diethylamine (0.82 ml, 585 mg, 8 mmol) was added CuI (30 mg, 0.08 mmol) and PdCl2(PPh3)2 (56 mg, 0.08 mmol). After stirring at room temperature for 5 h ethyl acetate was added and the solution was extracted with sat. ammonium chloride solution. The organic layer was dried (Na2SO4), filtered and evaporated. The resulting crude material was purified by flash chromatography using a cyclohexanes, ethyl acetate gradient (5%40%) on silica gel to afford the title compound (192 mg, 28%); UPLC: 0.88 min, MS: (ES/+) m/z: 427 [MH]+, C24H27FN2O4 requires 426.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with sat. ammonium chloride solution
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-564ca925f9bd422d8d91752fd767705f
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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