tert-butyl N-(1-carbamothioylpiperidin-4-yl)carbamate → Ethyl 2-(4-aminopiperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylate hydrochloride

HRID 2233892Notes

Reaction equation

HRID 2233892 reaction equation
[NH2:1][C:2]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10]C(=O)OC(C)(C)C)[CH2:6][CH2:5]1)=[S:3].[Cl:18][CH:19]([C:25](=O)[CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CCO>[ClH:18].[NH2:10][CH:7]1[CH2:6][CH2:5][N:4]([C:2]2[S:3][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:25]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[N:1]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 59296117tert-butyl N-(1-carbamothioylpiperidin-4-yl)carbamate2×HCID 86038328Ethyl 2-chloro-4-(2-methoxyethoxy)-3-oxobutanoate2×

Product 1

HCID 68579915Ethyl 2-(4-aminopiperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

tert-Butyl [1-(aminocarbonothioyl)piperidin-4-yl]carbamate (Intermediate 125, 400 mg) was dissolved in anhydrous EtOH (5 ml). Ethyl 2-chloro-4-(2-methoxyethoxy)-3-oxobutanoate (Intermediate 124, 368 mg) was added and the mixture was heated at 90° C. for 18 h. Partial removal of Boc group was detected. Solvent was removed in vacuo and the dried material was treated with 4 N HCl/dioxane for 2 h. Solvent was removed in vacuo to give a brown/yellow solid which was dried to afford the title compound which was used without further purification (508 mg).

Workup

  1. customPartial removal of Boc group
  2. customSolvent was removed in vacuo
  3. additionthe dried material was treated with 4 N HCl/dioxane for 2 h
  4. customSolvent was removed in vacuo
  5. customto give a brown/yellow solid which
  6. customwas dried

Sources & evidence

ORD record
ord-61cbc8f42d5c4c0ba076f7bea15964eb
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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