Diisopropylethylamine → HCID 178428186, compound

HRID 646913Notes

Reaction equation

HRID 646913 reaction equation
[O:1]=[S:2]1(=[O:22])[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([N:15]3[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16]3)[CH:9]=2)[CH2:4][CH2:3]1.[K+].[C:24]([C:26]1[N:27]=[C:28]([C:39]([O-])=[O:40])[N:29](COCC[Si](C)(C)C)[CH:30]=1)#[N:25].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[O:22]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:39]([C:28]3[NH:29][CH:30]=[C:26]([C:24]#[N:25])[N:27]=3)=[O:40])=[C:10]([N:15]3[CH2:16][CH2:17][CH:18]([CH3:21])[CH2:19][CH2:20]3)[CH:9]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 586384904-(1,1-Dioxo-hexahydro-1lambda6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenylamineHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 178428186HCID 178428186, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenylamine (as prepared in the previous step, 16 mg, 0.050 mmol), 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium (as prepared in Example 3, step (d), 17 mg, 0.055 mmol) and PyBroP (35 mg, 0.075 mmol) in 1 mL of DCM was added DIEA (17 μL, 0.10 mmol). The resulting mixture was stirred at RT for 20 h under Ar. Treated with 30 mL of EtOAc, the mixture was washed with H2O (3×10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1-2% EtOAc/DCM) gave 19 mg (68%) of the title compound as a colorless oil: 1H-NMR (CDCl3; 400 MHz): δ 10.4 (s, 1H), 8.29 (d, 1H, J=8.4 Hz), 7.79 (s, 1H), 7.02 (d, 1H, J=1.9 Hz), 6.99 (dd, 1H, J=8.4, 1.9 Hz), 5.97 (s, 2H), 3.67 (app t, 2H, J=8.3 Hz), 3.14 (m, 4H), 2.99 (d, 2H, J=12.0 Hz), 2.67-2.80 (m, 3H), 2.40 (m, 2H), 2.22 (m, 2H), 1.79 (m, 2H), 1.52-1.67 (m, 3H), 1.08 (d, 3H, J=5.9 Hz), 0.98 (app t, 2H, J=8.3 Hz), 0.001 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C28H41N5O4SSi, 572.3 (M+H), found 572.0.

Workup

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

Sources & evidence

ORD record
ord-b1aacb765abd453bbab860b2fb8e7a00
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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