Diisopropylethylamine → HCID 24964059, compound

HRID 1666382Notes

Reaction equation

HRID 1666382 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[N:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[C:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:17]=2)=[N:13][CH:14]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36](=O)[O:37]C2C=CC=CC=2)[N:30]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Br:8][C:9]1[CH:10]=[N:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[CH:22]=[C:23]2[CH2:28][CH2:27][N:26]([C:36]([NH:35][C:31]3[N:30]=[N:29][CH:34]=[CH:33][CH:32]=3)=[O:37])[CH2:25][CH2:24]2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20150036Phenyl pyridazin-3-ylcarbamateHCID 66876371HCID 66876371, compound

Product 1

HCID 24964059HCID 24964059, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyrimidine trifluoroacetate (0.315 mmol, from Step 5), in acetonitrile (1.5 mL) was treated with phenyl pyridazin-3-ylcarbamate (75 mg, 0.35 mmol) and diisopropylethylamine (0.192 mL, 1.10 mmol) and stirred at ambient temperature for 72 h. The reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel (0-10% ethanol (containing 11% aq NH4OH):dichloromethane) to afford the title compound (0.099 g, 67% yield) as a white foam. MS (APCI) M=466.0; 1H NMR (400 MHz, CDCl3) δ ppm 2.50 (t, J=5.56 Hz, 2H) 2.63 (t, J=5.65 Hz, 2H) 3.59-3.67 (m, 2H) 3.73 (t, J=4.39 Hz, 2H) 6.44 (s, 1H) 7.02-7.09 (m, 2H) 7.12 (d, J=7.60 Hz, 1H) 7.41 (t, J=7.90 Hz, 1H) 7.49 (dd, J=9.06, 4.58 Hz, 1H) 8.41-8.50 (m, 1H) 8.59 (s, 2H) 8.78 (br. s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (0-10% ethanol (containing 11% aq NH4OH):dichloromethane)

Sources & evidence

ORD record
ord-96da8351e640468282fe330be52e2680
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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