Diisopropylethylamine → HCID 67258244, compound

HRID 1476615Notes

Reaction equation

HRID 1476615 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:16][C:15]=1[C:25]([O-:27])=[O:26].[NH2:28][CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1.[CH3:42]CN(C(C)C)C(C)C>C1COCC1>[CH3:42][O:26][C:25]([C:15]1[S:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:18][C:14]=1[NH:13][C:2]([NH:28][CH:29]1[CH2:30][CH2:31][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:33][CH2:34]1)=[O:4])=[O:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 12682914-Amino-1-Boc-piperidineHCID 40963475HCID 40963475, compound

Product 1

HCID 67258244HCID 67258244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of triphosgene (421 mg) in THF (15 ml) under nitrogen atmosphere is added at 0° C. a solution of 3-amino-5-phenylthiophene-2-carboxylate (1.00 g) in THF (10 ml) within 2 h. The mixture is stirred at 0° C. for 1 h and at RT for additional 14 h. The resulting suspension is cooled to 0° C. and a solution tert-butyl 4-aminopiperidine-1-carboxylate (867 mg) in THF (10 ml) is added dropwise. After 15 min at 0° C. DIPEA (1.75 ml) is slowly added. The reaction mixture is stirred for 15 min at 0° C. and for 2.5 h at RT and then washed with an aqueous sodium chloride solution (5% w/w, three times with 20 ml each) and with brine (20 ml). The organic layer is dried over magnesium sulfate. All volatile materials are removed in vacuo to give the title compound as a solid.

Workup

  1. temperatureThe resulting suspension is cooled to 0° C.
  2. waitAfter 15 min at 0° C
  3. stirringThe reaction mixture is stirred for 15 min at 0° C. and for 2.5 h at RT
  4. washwashed with an aqueous sodium chloride solution (5% w/w, three times with 20 ml each) and with brine (20 ml)
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. customAll volatile materials are removed in vacuo

Sources & evidence

ORD record
ord-99ac9eed84794b14be3dea1d7b84c618
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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