Ethyl 4-piperidinecarboxylate → HCID 59627658, compound

HRID 1930157Notes

Reaction equation

HRID 1930157 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[C:21]([C:24]1[N:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([CH2:42][C:43](O)=[O:44])=[CH:38][C:37]=3[Cl:46])=[CH:32][CH:31]=2)[C:27]([CH3:47])=[N:26][C:25]=1[CH3:48])(=[O:23])[NH2:22].Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1>CN(C=O)C>[C:21]([C:24]1[N:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([CH2:42][C:43]([N:1]4[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]4)=[O:44])=[CH:38][C:37]=3[Cl:46])=[CH:32][CH:31]=2)[C:27]([CH3:47])=[N:26][C:25]=1[CH3:48])(=[O:23])[NH2:22]

Participants

7

Reactant 5

HCID 70770Ethyl 4-piperidinecarboxylateHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 498471732-(4'-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid

Product 1

HCID 59627658HCID 59627658, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of ethyl piperidine-4-carboxylate (90 mg, 0.57 mmol) and N-ethyl-N-isopropylpropan-2-amine (99 μL, 0.57 mmol) in DMF (342 μL) were treated with a solution of 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid (Example 1; 205 mg, 0.52 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (124 mg, 0.65 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (70.0 mg, 0.52 mmol) and N-ethyl-N-isopropylpropan-2-amine (99 μL, 0.57 mmol) in DMF (2049 μL) at RT. The resulting solution was stirred at RT for 20 hours. The reaction mixture was evaporated to dryness and redissolved in DCM (5 mL), and washed with water (5 mL). The organic layer was evaporated to afford ethyl 1-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetyl)piperidine-4-carboxylate (291 mg, 105%) which was used without further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in DCM (5 mL)
  3. washwashed with water (5 mL)
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-14dcb5e0c0ad494f8bfa89907c24d33f
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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