Tetrahydrofuran → 4-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1582146Notes

Reaction equation

HRID 1582146 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]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[O:25])=[N:19][C:18]=3[C:17]([O:32][CH3:33])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1>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]([N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[O:25])=[N:19][C:18]=3[C:17]([O:32][CH3:33])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 865888334-{4-methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 865888464-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl esterYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.13 g (0.274 mMol) of 4-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 6.0 ml of methanol and 6.0 ml of tetrahydrofuran 80.0 mg of Pd/C (10%) were added. The reaction mixture was hydrogenated at 60° C. for 8 h, then filtered and evaporated to dryness. The residue was subjected to column chromatography on silica gel (ethyl acetate) to yield 0.048 g (37%) 4-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester as a colorless foam. ES-MS m/e (%): 477 ([M+H]+, 100).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-332805c2a26346b9814b447b93036320
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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