Acetic Anhydride → Morpholine-4-carboxylic acid [7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-amide

HRID 1582121Notes

Reaction equation

HRID 1582121 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[S:12][C:8]=2[C:7]([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36].C(=O)(O)[O-].[Na+]>C1COCC1.O>[C:35]([N:25]1[CH2:24][CH:23]=[C:22]([C:7]2[C:8]3[S:12][C:11]([NH:13][C:14]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)=[O:15])=[N:10][C:9]=3[C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[CH2:27][CH2:26]1)(=[O:37])[CH3:36]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86588834Morpholine-4-carboxylic acid [4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-amide hydrochloride

Product 1

HCID 86588836Morpholine-4-carboxylic acid [7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-amideYield 76.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.04 g (0.097 mMol) morpholine-4-carboxylic acid [4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-amide hydrochloride in 2 ml THF were added 0.016 ml triethyl amine. At 0° C. 0.01 ml (0.11 mMol) acetic anhydride was added dropwise and stirred for 30 min. Then a mixture of 5 ml sat. aqueous sodium bicarbonate and 10 ml water were added. After extracting four times with 15 ml ethyl acetate the combined organic phases were dried over sodium sulfate and concentrated to dryness in vacuo to yield 0.031 g (76%) morpholine-4-carboxylic acid [7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-amide as a white solid. ES-MS m/e (%): 417 ([M+H]+, 100).

Workup

  1. customAt 0° C
  2. additionwere added
  3. extractionAfter extracting four times with 15 ml ethyl acetate the combined organic phases
  4. dry with materialwere dried over sodium sulfate
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-f73a62bcc8b4456bbc1dc9eff0e58172
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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