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

HRID 1582131Notes

Reaction equation

HRID 1582131 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(C(C)C)C(C)C)C.[Cl:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][N:44]=1)[C:39](Cl)=[O:40].CO>C1COCC1.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:42]=[CH:43][N:44]=[C:36]([Cl:35])[CH:37]=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

7

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 207255094-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 865888414-{2-[(2-chloro-pyridine-4-carbonyl)-amino]-4-methoxy-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 89.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.25 g (0.69 mMol) 4-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 10 ml THF were added 0.26 ml ethyl diisopropyl amine and 0.16 g (0.76 mMol) 2-chloro-isonicotinoyl chloride, dissolved in 5 ml of dichloro methane. The reaction mixture was stirred at room temperature for 16 h. Then 5 ml methanol were added. The solvent was evaporated to dryness, the residue taken up in ethyl acetate 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/hexane 1:1) to yield 0.308 g (89%) of 4-{2-[(2-chloro-pyridine-4-carbonyl)-amino]-4-methoxy-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a yellow foam. ES-MS m/e (%): 501 ([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-6ab11f82d44847929c68e94f33576d12
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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