Diisopropylamine → HCID 59513421, compound

HRID 1041897Notes

Reaction equation

HRID 1041897 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:15](=[O:16])[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=3)([CH3:17])[NH:13][C:12]2=[O:25])[CH:5]=1.[C:27]([NH:37][CH2:38][C:39]#[CH:40])([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].N(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.[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>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:15](=[O:16])[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:40]#[C:39][CH2:38][NH:37][C:27]([O:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[O:28])[CH:19]=3)([CH3:17])[NH:13][C:12]2=[O:25])[CH:5]=1

Participants

8

Reactant 3

HCID 7912DiisopropylamineHCID 11137906Benzyl prop-2-yn-1-ylcarbamateHCID 45605619HCID 45605619, compound

Product 1

HCID 59513421HCID 59513421, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of hydantoin 2 (830 mg, 2 mmol), N-Cbz-propargylamine (460 mg, 2.43 mmol; prepared according to the literature by Yasuda et al., patent application 2003, US 2003/0004353), CuI (20 mg, 0.1 mmol), PdCl2(PPh3)2 (70 mg, 0.1 mmol) and iPr2NH (850 μL, 6 mmol) in DMF (5 mL) was heated for 15 min at 100° C. (Smith Microwave Synthesizer). The reaction mixture was diluted with EtOAc, washed with 1 M HCl (2×), NaHCO3 (1×), water (3×) and brine (1×), then dried over MgSO4, filtered and concentrated under vacuum. The crude material was subjected to silica gel chromatography (30→50% EtOAc/hexanes) to yield the desired material as a colorless film (598 mg, 57%). 1H NMR (400 MHz, CDCl3) δ 7.89 (m, 2H), 7.21-7.46 (m, 12H), 6.71 (bs, 1H), 4.62 (s, 2H), 4.12 (m, 2H), 3.81 (s, 3H), 1.72 (s, 3H). MS (ES+): 526 (M+H).

Workup

  1. customprepared
  2. washwashed with 1 M HCl (2×), NaHCO3 (1×), water (3×) and brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-509bb710aa314fc7b5df33823379e0f7
Source dataset
uspto-grants-2013_10
Patent number
US08557798B2

Reaction notes

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