Diisopropylethylamine → (1-{4-[Methyl-(tetrahydro-pyran-4-carbonyl)-amino]-benzenesulfonyl}-piperidin-4-yl)-carbamic acid tert-butyl ester

HRID 337212Notes

Reaction equation

HRID 337212 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[O:35]1[CH2:40][CH2:39][CH:38]([C:41](Cl)=[O:42])[CH2:37][CH2:36]1>C1COCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([N:23]([CH3:24])[C:41]([CH:38]3[CH2:39][CH2:40][O:35][CH2:36][CH2:37]3)=[O:42])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2795505Oxane-4-carbonyl chlorideHCID 71060136[1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 71060228(1-{4-[Methyl-(tetrahydro-pyran-4-carbonyl)-amino]-benzenesulfonyl}-piperidin-4-yl)-carbamic acid tert-butyl esterYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.13 g, 0.35 mmol) was dissolved in THF (5 ml). To this was added diisopropylethylamine (0.18 ml, 0.7 mmol) in one portion followed by the drop wise addition of tetrahydro-2H-pyran-4-carbonyl chloride (0.06 ml, 0.38 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was concentrated, diluted with DCM (200 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.17 g, 98% yield) as a white powder which was taken on without further purification. Tr=1.89 min m/z (ES+) (M+Na+) 504.

Workup

  1. concentrationAfter this time the mixture was concentrated
  2. additiondiluted with DCM (200 ml)
  3. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-53cebd2059fb423499af9799a08148ee
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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