Diisopropylethylamine → HCID 71079542, compound

HRID 337207Notes

Reaction equation

HRID 337207 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[CH:24]1([C:27]([N:29]2[C:37]3[C:32](=[CH:33][C:34]([S:38](Cl)(=[O:40])=[O:39])=[CH:35][CH:36]=3)[CH2:31][CH2:30]2)=[O:28])[CH2:26][CH2:25]1>C(Cl)Cl>[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:38]([C:34]2[CH:33]=[C:32]3[C:37](=[CH:36][CH:35]=2)[N:29]([C:27]([CH:24]2[CH2:25][CH2:26]2)=[O:28])[CH2:30][CH2:31]3)(=[O:39])=[O:40])[CH2:19][CH2:18]1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 201094621-CYCLOPROPANECARBONYL-2,3-DIHYDRO-1H-INDOLE-5-SULFONYL CHLORIDE

Product 1

HCID 71079542HCID 71079542, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.33 ml, 2.0 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (0.2 g, 1.0 mmol) in DCM (5 ml) at room temperature. To this mixture was added 1-cyclopropanecarbonyl-2,3-dihydro-1H-indole-5-sulfonyl chloride (0.29 g, 1.0 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was diluted with DCM (100 ml) and washed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting solid was collected by filtration, dried with diethyl ether and dried under vacuum give the title compound (0.36 g, 73% yield) as a pale yellow solid. Tr=2.02 min m/z (ES+) (M+Na+) 472.

Workup

  1. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe resulting solid was collected by filtration
  7. dry with materialdried with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3803567d6395441ea1072359d014d073
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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