Diisopropylethylamine → HCID 24963708, compound

HRID 1666369Notes

Reaction equation

HRID 1666369 reaction equation
FC(F)(F)C(O)=O.N1[CH2:13][CH2:12][C:11](=[C:14]2[CH:28]=[CH:27][CH:26]=[C:16]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][N:19]=3)[CH:15]2C)CC1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([NH:36][C:37](=[O:45])OC2C=CC=CC=2)[CH:31]=1.[CH:46]([N:49](C(C)C)[CH2:50]C)(C)[CH3:47]>CS(C)=O>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][C:16]2[CH:15]=[C:14]([CH:28]=[CH:27][CH:26]=2)[CH:11]=[C:12]2[CH2:13][CH2:50][N:49]([C:37]([NH:36][C:32]3[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=3)=[O:45])[CH2:46][CH2:47]2)=[N:19][CH:20]=1)#[N:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66875977HCID 66875977, compound

Product 1

HCID 24963708HCID 24963708, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(3-piperidin-4-ylidene-methyl-phenoxy)-5-cyanopyridine trifluoroacetate (0.280 g, 0.72 mmol) and phenyl pyridin-3-ylcarbamate (0.154 g, 0.72 mmol) in DMSO (2.0 mL) was treated with diisopropylethylamine (0.170 g, 1.6 mmol) and heated to 60° C. After 3 h, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (5% of 1N NH3 in MeOH, in dichloromethane) to afford the title compound (155 mg, 52%) as white crystals after trituration in diethyl ether. MS (APCI 10V) AP+ 412.16; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (t, J=5.46 Hz, 2H) 2.45 (t, J=5.46 Hz, 2H) 3.46 (t, J=5.46 Hz, 2H) 3.54 (t, J=5.46 Hz, 2H) 6.39 (s, 1H) 7.02-7.04 (m, 2H) 7.12 (d, J=7.60 Hz, 1H) 7.21 (d, J=8.20, Hz, 1H) 7.25-7.27 (m, 1H) 7.39 (t, J=8.01 Hz, 1H) 7.83 (dd, J=5.28 Hz, 2.74 Hz, 2H) 8.10 (d, J=2.86 Hz, 1H) 8.25 (s, 1H) 8.30 (s, 1H) 8.8 (m, 1H) 8.75 (s, 1H).

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (5% of 1N NH3 in MeOH, in dichloromethane)

Sources & evidence

ORD record
ord-89c9173c758141f89ec0e9918d488d6b
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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