Tetrahydrofuran → HCID 86588844, compound

HRID 1582136Notes

Reaction equation

HRID 1582136 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]([C:26]4[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28](Cl)[CH:27]=4)=[O:25])=[N:19][C:18]=3[C:17]([O:35][CH3:36])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.C(N(CC)CC)C>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]([C:26]4[CH:27]=[CH:28][N:29]=[C:30]([O:32][CH3:33])[CH:31]=4)=[O:25])=[N:19][C:18]=3[C:17]([O:35][CH3:36])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 865888454-{2-[(2-chloro-6-methoxy-pyridine-4-carbonyl)-amino]-4-methoxy-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86588844HCID 86588844, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.39 g (0.73 mMol) of 4-{2-[(2-chloro-6-methoxy-pyridine-4-carbonyl)-amino]-4-methoxy-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 16.0 ml of methanol and 16.0 ml THF 100 mg of Pd/C (10%) and 0.15 ml triethyl amine were added. The reaction mixture was hydrogenated at 60° C. for 6 h, then filtered and evaporated to dryness in vacuo. The residue was subjected to column chromatography (ethyl acetate/hexane 1:1) to yield 0.110 g (30%) 4-{4-methoxy-2-[(2-methoxy-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester as a white foam. ES-MS m/e (%): 499 ([M+H]+, 100).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a293a2555d6847cfb9346d2687aa4a50
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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