Benzyl chloroformate → HCID 54577790, compound

HRID 1845909Notes

Reaction equation

HRID 1845909 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:5]2[CH:14]=[CH:15][C:16]([C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#[N:21])=[CH:17][C:4]=2[S:3]1.CCN(C(C)C)C(C)C.[CH:35]1[CH:40]=[CH:39][C:38]([CH2:41][O:42][C:43](Cl)=[O:44])=[CH:37][CH:36]=1>O1CCOCC1.CO>[C:20]([C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=1[C:16]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:7][CH:8]3[CH2:9][CH2:10][N:11]([C:43]([O:42][CH2:41][C:38]4[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=4)=[O:44])[CH2:12][CH2:13]3)[C:2](=[O:1])[S:3][C:4]=2[CH:17]=1)#[N:21]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 54577789HCID 54577789, compound

Product 1

HCID 54577790HCID 54577790, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial was added 2-[2-oxo-3-(piperidin-4-ylmethyl)-2,3-dihydro-1,3-benzothiazol-6-yl]benzonitrile (11-3) (HCl salt) (0.025 g, 0.065 mmol), dissolved in 3 mL of anhydrous 1,4 Dioxane, then added DIPEA (0.034 mL, 0.194 mmol), followed by benzyl chloridocarbonate (0.014 mL, 0.097 mmol). The reaction mixture was then stirred at room temperature for 1 hour. The crude reaction mixture was then diluted with methanol, filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) gave benzyl 4-{[6-(2-cyanophenyl)-2-oxo-1,3-benzothiazol-3(2H)-yl]methyl}piperidine-1-carboxylate (12-1) as waxy solid. HRMS (M+H)+: observed=484.1700, calculated=484.1689.

Workup

  1. customThe crude reaction mixture
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification of crude
  5. customreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water)

Sources & evidence

ORD record
ord-e69ab34651674405b5f695f6598ac5fd
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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