Sodium Cyanate → HCID 69694583, compound

HRID 489908Notes

Reaction equation

HRID 489908 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]([N:29]5[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)=[O:28])[CH2:22]4)[CH2:17][CH2:16]3)=[O:14])[CH:10]=[C:9]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-:41][C:42]#[N:43].[Na+]>O.C(O)CC.O1CCOCC1>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([N:15]3[CH2:16][CH2:17][CH:18]([N:21]4[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]([N:29]5[CH2:34][CH2:33][N:32]([C:42]([NH2:43])=[O:41])[CH2:31][CH2:30]5)=[O:28])[CH2:22]4)[CH2:19][CH2:20]3)=[O:14])[CH:10]=[C:9]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 517096Sodium Cyanate2×HCID 23589145HCID 23589145, compound

Product 1

HCID 69694583HCID 69694583, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 19902870HCID 19902870, compoundSolvent

Procedure

(3R)-(2,6-Diphenyl-pyridin-4-yl)-[3-(piperazine-1-carbonyl)-[1,4′]bipiperidinyl-1′-yl]-methanone (21.4 mg, 0.040 mmol) and sodium cyanate (0.060 mmol, 3.9 mg) were heated at 100° C. in a water-dioxane-n-propanol solution. After 2 h an additional aliquot of sodium cyanate (4 mg) was added and heating was continued for another 1 hour then the solution was allowed to stir at ambient temperature for an additional 42 h. The solvent was removed under vacuum and the product was purified by silica gel chromatography eluting with a 5% to 10% methanol-dichloromethane gradient to give the title compound (9.3 mg, 40%).

Workup

  1. temperatureheating
  2. customThe solvent was removed under vacuum
  3. customthe product was purified by silica gel chromatography
  4. washeluting with a 5% to 10% methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-34a0bbc4970149b29e38ce7bcfa43d1e
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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