Diisopropylethylamine → HCID 59128589, compound

HRID 1428063Notes

Reaction equation

HRID 1428063 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([C:16]([OH:18])=O)[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1)#[N:2].[K+].C(C1N=C(C([O-])=O)N(COCC[Si](C)(C)C)C=1)#N.CCN(C(C)C)C(C)C.[C:47]1([C:53]2[CH:58]=[C:57]([CH:59]3[CH2:64][CH2:63][N:62]([O:65][CH3:66])[CH2:61][CH2:60]3)[CH:56]=[CH:55][C:54]=2[NH2:67])[CH2:52][CH2:51][CH2:50][CH2:49][CH:48]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:47]1([C:53]2[CH:58]=[C:57]([CH:59]3[CH2:64][CH2:63][N:62]([O:65][CH3:66])[CH2:61][CH2:60]3)[CH:56]=[CH:55][C:54]=2[NH:67][C:16]([C:5]2[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[CH:7]=[C:3]([C:1]#[N:2])[N:4]=2)=[O:18])[CH2:52][CH2:51][CH2:50][CH2:49][CH:48]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 591285854-Cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acidHCID 59128594HCID 59128594, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 59128589HCID 59128589, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid, potassium salt (as prepared in Example 3, step (d), 35.6 mg, 0.100 mmol), DIEA (0.34 μL, 0.20 mmol), 2-cyclohex-1-enyl-4-(1-methoxy-piperidin-4-yl)-phenylamine (as prepared in previous step, 28.6 mg, 0.1 mmol) and PyBroP (69.9 mg, 0.150 mmol) in DCM (2 mL) was stirred at RT for 12 h. The reaction mixture was diluted with DCM (10 mL) and washed with saturated aqueous NaHCO3 (10 mL) and water (10 mL). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The product was chromatographed on silica (20-40% EtOAc/hexane) to obtain the title compound (26 mg, 48%). Mass spectrum (ESI, m/z): Calcd. for C29H41N5O3Si, 536.3 (M+H). found 536.2.

Workup

  1. washwashed with saturated aqueous NaHCO3 (10 mL) and water (10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe product was chromatographed on silica (20-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-5da5ccbd79934e6293a86469b3c72da4
Source dataset
uspto-grants-2015_01
Patent number
US08933091B2

Reaction notes

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