Diethyl Pyrocarbonate → HCID 90384328, compound

HRID 1479850Notes

Reaction equation

HRID 1479850 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:18][CH3:19])[C:12]2([C:15](O)=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[F:31][C:32]([F:49])([F:48])[O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[C:44]([CH2:46][NH2:47])[CH:43]=[CH:42][N:41]=2)=[CH:36][CH:35]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:18][CH3:19])[C:12]2([C:15]([NH:47][CH2:46][C:44]3[CH:43]=[CH:42][N:41]=[C:40]([C:37]4[CH:36]=[CH:35][C:34]([O:33][C:32]([F:49])([F:31])[F:48])=[CH:39][CH:38]=4)[CH:45]=3)=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 68759664[2-[4-(Trifluoromethoxy)phenyl]-4-pyridyl]methanamineHCID 131736596HCID 131736596, compound

Product 1

HCID 90384328HCID 90384328, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acid 15B (303 mg, 1 mmol) was dissolved in 5 ml of THF and at rt DEPC (1.1 equiv, 0.17 ml) and [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (1.1 equiv., 295 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (3:7 EtOAc:Petroleum ether) afforded 100 mg of a white solid. Yield=18% 1HNMR (DMSO, 200 MHz) δ 1.12 (2H, bs), 1.22 (3H, t, J=7.2 Hz), 1.40 (2H, bs), 3.40 (2H, q, J=4.8 Hz), 4.41 (2H, d, J=5.4 Hz), 7.26 (1H, dd, J=3.8 Hz), 7.49 (2H, d, J=8 Hz), 7.65 (2H, dd, J=8.6 Hz), 7.84 (2H, dd, J=6.8 Hz, J′=1.6 Hz), 7.90 (1H, bs), 8.20 (2H, dd, J=6.8 Hz, J′=1.8 Hz), 8.28 (1H, t), 8.59 (1H, d, J=5.2 Hz) [M+1] 553.9 (C25H23ClF3N3O4S requires 553.98).

Workup

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionThe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (3:7 EtOAc:Petroleum ether)

Sources & evidence

ORD record
ord-2b4699cd4d0c48b296bb4338f66716c5
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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