Diisopropylethylamine → HCID 58994986, compound

HRID 536947Notes

Reaction equation

HRID 536947 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([C:20]4[N:21]=[N:22][NH:23][N:24]=4)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH2:25])=[CH:4][CH2:3]1.[K+].[C:28]([C:30]1[N:31]=[C:32]([C:43]([O-])=[O:44])[N:33]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:34]=1)#[N:29].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([C:20]4[N:21]=[N:22][NH:23][N:24]=4)[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH:11]=[CH:10][C:9]=2[NH:25][C:43]([C:32]2[N:33]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:34]=[C:30]([C:28]#[N:29])[N:31]=2)=[O:44])=[CH:4][CH2:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylateHCID 68835220HCID 68835220, compound

Product 1

HCID 58994986HCID 58994986, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the crude product of 2-(4,4-dimethyl-cyclohex-1-enyl)-4-[4-(2H-tetrazol-5-yl)-tetrahydro-pyran-4-yl]-phenylamine (76 mg, ca. 0.22 mmol) in 2.5 mL of DMF was added potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 1, step (d), 72 mg, 0.24 mmol), PyBroP (110 mg, 0.236 mmol) and DIEA (112 μL, 0.645 mmol). After stirring at RT for 2 d, the mixture was treated with 20 mL of H2O and extracted with EtOAc (2×20 mL). The combined organic layers were washed with H2O (2×10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (1-3 MeOH/DCM) to afford the title compound (55 mg, 42% for 2 steps) as a faint brown solid. Mass spectrum (ESI, m/z): Calcd. for C31H42N8O3Si, 603.3 (M+H). found 602.9.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic layers were washed with H2O (2×10 mL) and brine (10 mL)
  3. dry with materialAfter drying over Na2SO4
  4. concentrationconcentrating in vacuo
  5. customthe residue was purified by silica gel chromatography (1-3 MeOH/DCM)

Sources & evidence

ORD record
ord-b86415de73f14adbba826290000ab2dd
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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