2-Chloroethyl isocyanate → HCID 59625574, compound

HRID 2192823Notes

Reaction equation

HRID 2192823 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([C:13]([C:15]2[C:16]([NH:25][CH2:26][CH2:27][CH2:28][S:29][CH3:30])=[N:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[N:19][CH:20]=2)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][N:4]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:3]1.Cl[CH2:39][CH2:40][N:41]=[C:42]=[O:43].CC(C)([O-])C.[K+]>C1COCC1.O>[C:21]([C:18]1[N:17]=[C:16]([NH:25][CH2:26][CH2:27][CH2:28][S:29][CH3:30])[C:15]([C:13]([N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C@H:6]2[CH2:7][C@@H:2]([N:1]3[CH2:39][CH2:40][NH:41][C:42]3=[O:43])[CH2:3][N:4]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH2:5]2)=[O:14])=[CH:20][N:19]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 160352-Chloroethyl isocyanateHCID 23665647Potassium tert-butoxideHCID 59625415HCID 59625415, compound

Product 1

HCID 59625574HCID 59625574, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (3R,5S)-3-amino-5-{[(2-tert-butyl-4-{[3-(methylsulfanyl)propyl]amino}pyrimidin-5-yl)carbonyl](2-methylpropyl)amino}piperidine-1-carboxylate (124 mg) was dissolved in THF (4 ml), chloroethyl isocyanate (24 μl) was added, and the mixture was stirred at room temperature for 1 hr. Potassium tert-butoxide (40 mg) was added and the reaction mixture was stirred at room temperature for 7 hr and further at 60° C. for 5 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (10:90-100:0) and concentrated under reduced pressure to give the object compound (70.3 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 7 hr and further at 60° C. for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washeluted with ethyl acetate-hexane (10:90-100:0)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6abe3be08f024d7b81ba7cc702598c2e
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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