4-(N-Boc-amino)piperidine → [1-(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 550823Notes

Reaction equation

HRID 550823 reaction equation
C1(O[C:8](=[O:21])[NH:9][C:10]2[S:11][C:12]3[N:13]=[CH:14][N:15]=[C:16]([O:19][CH3:20])[C:17]=3[N:18]=2)C=CC=CC=1.[C:22]([O:26][C:27](=[O:35])[NH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([CH3:25])([CH3:24])[CH3:23]>C(#N)C>[C:22]([O:26][C:27](=[O:35])[NH:28][CH:29]1[CH2:34][CH2:33][N:32]([C:8](=[O:21])[NH:9][C:10]2[S:11][C:12]3[N:13]=[CH:14][N:15]=[C:16]([O:19][CH3:20])[C:17]=3[N:18]=2)[CH2:31][CH2:30]1)([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 7238334-(N-Boc-amino)piperidineHCID 59011944(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl ester

Product 1

HCID 59011963[1-(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 90.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl ester (6 g, 19.8 mmol) and piperidin-4-yl-carbamic acid tert-butyl ester (4.37 g, 21.8 mmol) in acetonitrile (400 mL) was heated to reflux for 1 h and was then stirred at 25° C. overnight. The resulting solid was collected by filtration, rinsed with acetonitrile and dried in vacuo to afford [1-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (7.3 g, 90%) as a white solid; ES-HRMS m/e calcd for C17H24N6O4S (M+H)+ 409.1653, found 409.1653.

Workup

  1. temperatureto reflux for 1 h
  2. filtrationThe resulting solid was collected by filtration
  3. washrinsed with acetonitrile
  4. customdried in vacuo

Sources & evidence

ORD record
ord-765818d252354ee89b17c56cc537cafb
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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