Triethylamine → tert-Butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 2199173Notes

Reaction equation

HRID 2199173 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[S:22][CH:23]=[C:24]([C:26]([OH:28])=O)[N:25]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[Cl-].[CH3:30][O:31][NH2+:32][CH3:33].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1.O>[CH3:30][O:31][N:32]([CH3:33])[C:26]([C:24]1[N:25]=[C:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:20][CH2:19]2)[S:22][CH:23]=1)=[O:28]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27955312-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)-1,3-thiazole-4-carboxylic acidHCID 11040634Methoxy(methyl)azanium;chloride

Product 1

HCID 86660504tert-Butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

At room temperature, triethylamine (324 mg) was added to a suspension of 2-[1-(tert-butoxycarbonyl)piperidin-4-yl]-1,3-thiazole-4-carboxylic acid (1.0 g) in dichloromethane (30 mL). After ten minutes of stirring, methoxy(methyl)ammonium chloride (312 mg), 4-dimethylaminopyridine (39 mg) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide HCl salt (675 mg) were added. The mixture was stirred at room temperature overnight, and water was then added. The aqueous phase was separated off and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue was purified chromatographically. This gave tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.0 g).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe aqueous phase was separated off
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-5e96555ae5634a62aeee7f61e18fe0fb
Source dataset
uspto-grants-2016_06
Patent number
US09357779B2

Reaction notes

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