Ethyl isocyanate → HCID 131732949, compound

HRID 2171689Notes

Reaction equation

HRID 2171689 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([F:30])=[C:12]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH2:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[CH2:31]1[CH2:35][O:34]CC1.[CH2:36]([N:38]=C=O)[CH3:37].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CCOC(C)=O.O>[CH2:36]([NH:38][C:35]([CH2:31][N:27]1[CH2:26][CH2:25][CH:24]([CH2:23][O:22][C:19]2[N:18]=[CH:17][C:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][OH:8])[C:11]=3[F:30])=[CH:21][N:20]=2)[CH2:29][CH2:28]1)=[O:34])[CH3:37]

Participants

7

Reactant 4

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 11078149TBAF tetrahydrofuranHCID 89601110HCID 89601110, compound

Product 1

HCID 131732949HCID 131732949, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-2-(piperidin-4-ylmethoxy)pyrimidine (200 mg) was mixed with THF (4 ml), and ethylisocyanate (91 mg) was added thereto, followed by stirring at room temperature overnight. A 1M TBAF/THF solution (1 ml) was added to the reaction mixture, followed by further stirring at room temperature for 3 hours. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (MeOH/CHCl3) to obtain N-ethyl-4-[({5-[2-fluoro-3-(hydroxymethyl)phenyl]pyrimidin-2-yl}oxy)methyl]piperidine-1-carboxyamide (159.3 mg).

Workup

  1. additionwas added
  2. stirringby further stirring at room temperature for 3 hours
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (MeOH/CHCl3)

Sources & evidence

ORD record
ord-60e03362e2a64fdd92d3039c6007f1a0
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

Loading…