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

HRID 1582119Notes

Reaction equation

HRID 1582119 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].O1CCOCC1.C(N(CC)CC)C.[N:39]1([C:45](Cl)=[O:46])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>O>[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:45]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[O:46])=[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 8471TriethylamineHCID 312751,4-DioxaneHCID 848104-Morpholinecarbonyl chlorideHCID 207255094-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 865888334-{4-methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.15 g (0.42 mMol) 4-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 5 ml dioxane 44 mg (1.0 mMol) NaH (dispersion in mineral oil 60%) were added and stirred for 1 h at room temperature. Then 0.174 ml (1.24 mMol) triethyl amine and 0.114 ml (1.0 mMol) morpholine-4-carbonyl chloride were added and stirred for 16 h at room temperature. After addition of 10 ml water the mixture was extracted three times with 15 ml ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated to dryness in vacuo. The residue was subjected to column chromatography (ethyl acetate) to yield 0.135 g (69%) 4-{4-methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a colorless foam. ES-MS m/e (%): 475 ([M+H]+, 100).

Workup

  1. additionwere added
  2. stirringstirred for 16 h at room temperature
  3. extractionwas extracted three times with 15 ml ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-25b3351a911d4ec389ee35c3f7108d0d
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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