Diisopropylethylamine → HCID 59771303, compound

HRID 340572Notes

Reaction equation

HRID 340572 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([C:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=2)[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].[K+].[C:24]([C:26]1[N:27]=[C:28]([C:39]([O-])=[O:40])[N:29]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:30]=1)#[N:25].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:39]([C:28]2[N:29]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:30]=[C:26]([C:24]#[N:25])[N:27]=2)=[O:40])=[C:11]([C:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=2)[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 59771183HCID 59771183, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 59771303HCID 59771303, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(4-amino-3-cyclohex-1-enyl-phenyl)-malonic acid dimethyl ester (as prepared in the previous step, 100 mg, 0.330 mmol), potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 1, step (d), 106 mg, 0.346 mmol) and bromotripyrrolidinophosphonium hexafluoro-phosphate (PyBroP) (154 mg, 0.330 mmol) in 3 mL of DMF was added N,N-diisopropylethylamine (DIEA) (0.172 mL, 0.990 mmol). After stirring at RT for 16 h, the mixture was treated with 50 mL of EtOAc and washed with H2O (2×15 mL), brine (15 mL) and dried (Na2SO4). The organic solvent was evaporated and the residue was purified by flash chromatography on silica gel (5-10% EtOAc-hexane) to give 118 mg (85%) of the title compound as a colorless oil: Mass spectrum (ESI, m/z): Calcd. for C28H36N4O6Si, 553.2 (M+H). found 552.6.

Workup

  1. washwashed with H2O (2×15 mL), brine (15 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe organic solvent was evaporated
  4. customthe residue was purified by flash chromatography on silica gel (5-10% EtOAc-hexane)

Sources & evidence

ORD record
ord-27a88e26025d4c4f8ef10a1b05c53d9c
Source dataset
uspto-grants-2014_11
Patent number
US08895584B2

Reaction notes

Loading…