Diisopropylethylamine → HCID 58754884, compound

HRID 1711236Notes

Reaction equation

HRID 1711236 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=2[NH2:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[K+].[C:18]([C:20]1[N:21]=[C:22]([C:33]([O-])=[O:34])[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)#[N:19].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]([CH3:14])[CH3:15])[CH:10]=[CH:9][C:8]=2[NH:16][C:33]([C:22]2[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=[C:20]([C:18]#[N:19])[N:21]=2)=[O:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 58754886HCID 58754886, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 58754884HCID 58754884, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-cyclohex-1-enyl-4-isopropyl-phenylamine (as prepared in the previous step, 30.0 mg, 0.139 mmol), potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 11, step (d), 43.0 mg, 0.141 mmol) and PyBroP (65.0 mg, 0.139 mmol) in 1.5 mL of DMF was added DIEA (73 μL, 0.417 mmol). The resulting mixture was stirred at RT for 16 h under Ar. Treated with 30 mL of EtOAc, the mixture was washed with H2O (2×10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (DCM) gave 55.4 mg (86%) of the title compound as a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C26H36N4O2Si, 465.3 (M+H), found 464.9.

Workup

  1. washthe mixture was washed with H2O (2×10 mL), brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2abc6745cba942278106f7f8d21f243f
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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