Methanol → HCID 149433996, compound

HRID 1947263Notes

Reaction equation

HRID 1947263 reaction equation
[C:1]([C:3]1([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].ClC(Cl)(Cl)[C:26]([N:28]=C=O)=[O:27].C(N(CC)CC)C.CO>C(Cl)Cl.O>[NH:2]=[C:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[N:16]([C:17]2[CH:18]=[CH:19][C:20]([I:23])=[CH:21][CH:22]=2)[C:26](=[O:27])[NH:28]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 66791326HCID 66791326, compound

Product 1

HCID 149433996HCID 149433996, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 4-cyano-4-[(4-iodophenyl)amino]piperidine-1-carboxylate (22 g, 51.5 mmol) in DCM (150 mL) was added trichloroacetylisocyanate (6.12 mL, 51.5 mmol) dropwise. After stirring at rt for 1 h30, triethylamine (7.18 mL, 51.5 mmol), water (4.64 mL, 257.5 mmol) and methanol (10.43 mL, 257.5 mmol), and the reaction mixture was stirred at 40° C. for 3 h, cooled to rt, diluted with water (200 mL), and a purple solid was filtered on paper, washed with water and a small amount of DCM, and air dried to afford the desired product as a white solid. LRMS (M+1)=471.

Workup

  1. temperaturecooled to rt
  2. filtrationa purple solid was filtered on paper
  3. washwashed with water
  4. dry with materiala small amount of DCM, and air dried

Sources & evidence

ORD record
ord-fb22da2cbbb74d309a6d71ff44e4b4ec
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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