Diisopropylethylamine → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-[2-(2-dimethylamino-ethyl)-2H-tetrazol-5-ylmethyl]-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide

HRID 1711310Notes

Reaction equation

HRID 1711310 reaction equation
[CH3:1][C:2]1([CH3:38])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH:11]=[CH:10][C:9]=2[NH:20][C:21]([C:23]2[N:24]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)=[O:22])=[CH:4][CH2:3]1.Cl.Cl[CH2:41][CH2:42][N:43]([CH3:45])[CH3:44].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:44][N:43]([CH3:45])[CH2:42][CH2:41][N:17]1[N:18]=[N:19][C:15]([CH2:14][C:12]2[CH:11]=[CH:10][C:9]([NH:20][C:21]([C:23]3[N:24]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:37])[CH3:36])[CH:25]=[C:26]([C:28]#[N:29])[N:27]=3)=[O:22])=[C:8]([C:5]3[CH2:6][CH2:7][C:2]([CH3:38])([CH3:1])[CH2:3][CH:4]=3)[CH:13]=2)=[N:16]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178424487HCID 178424487, compound

Product 1

HCID 587548324-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-[2-(2-dimethylamino-ethyl)-2H-tetrazol-5-ylmethyl]-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amideYield 24.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(1H-tetrazol-5-ylmethyl)-phenyl]-amide (as prepared in Example 42, step (b), 78 mg, 0.14 mmol) and (2-chloro-ethyl)-dimethyl-amine hydrochloride (63 mg, 0.43 mmol) in DMF (1 mL) was treated with DIEA (128 μL, 0.73 mmol) and then heated at 100° C. for 1 h. The reaction was allowed to cool to room temperature, diluted with EtOAc (25 mL) and then washed with water (2×10 mL). The organic phase was dried (Na2SO4) and concentrated in vacuo. Purification by preparative tlc (10% MeOH—CHCl3) afforded 21 mg (24%) of the title compound. Mass spectrum (ESI, m/z): Calcd. for C31H45N9O2Si, 604.3 (M+H), found 604.1.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with water (2×10 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by preparative tlc (10% MeOH—CHCl3)

Sources & evidence

ORD record
ord-76a8c0313a4b4a36b9bbe971029ba40b
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

Loading…