Methanol → 4-{4-methoxy-2-[(2-methyl-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1582148Notes

Reaction equation

HRID 1582148 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]([NH2:23])=[N:19][C:18]=3[C:17]([O:24][CH3:25])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:28]([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])C)C.CO.C1C[O:40][CH2:39][CH2:38]1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:39]([C:38]4[CH:31]=[CH:29][N:28]=[C:32]([CH3:33])[CH:34]=4)=[O:40])=[N:19][C:18]=3[C:17]([O:24][CH3:25])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 207255094-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 865888384-{4-methoxy-2-[(2-methyl-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.35 g (0.97 mMol) 4-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 20 ml THF were added 0.365 ml ethyl diisopropyl amine and 0.2 g (1.10 mMol) 4-(2-chloromethyl)-isonicotinic acid chloride, dissolved in 10 ml dichloro methane. The reaction mixture was stirred at room temperature for 72 h. Then 5 ml methanol were added. The solvent was evaporated to dryness, the residue taken up in dichloro methane and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated to dryness in vacuo. The residue was subjected to column chromatography (ethyl acetate) to yield 0.32 g (69%) of 4-{4-methoxy-2-[(2-methyl-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a dark brown solid. ES-MS m/e (%): 481 ([M+H]+, 100).

Workup

  1. customThe solvent was evaporated to dryness
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-574a6e49bb1d45429306294527d2bd2e
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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