Tetrahydrofuran → 4-[2-(4-Fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1582123Notes

Reaction equation

HRID 1582123 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[N:19][C:18]=3[C:17]([O:33][CH3:34])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)=[N:19][C:18]=3[C:17]([O:33][CH3:34])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 865888324-[2-(4-fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 865888374-[2-(4-Fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.14 g (0.94 mmol) of 4-[2-(4-fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 6.0 ml of methanol and 6.0 ml THF 90.0 mg of Pd/C (10%) were added. The reaction mixture was hydrogenated at 60° C. for 4 h, then filtered and evaporated to dryness in vacuo. The residue was crystallized from diethyl ether to yield 0.105 g (75%) 4-[2-(4-fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid tert-butyl ester as a white solid. F.p.: 222-223° C.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness in vacuo
  3. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-3f15680fc9f4418995c7ad4e88f483d9
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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