Acetic Anhydride → N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-2-methyl-isonicotinamide

HRID 1582128Notes

Reaction equation

HRID 1582128 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([NH:13][C:14](=[O:22])[C:15]3[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=3)[S:12][C:8]=2[C:7]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37].C(=O)(O)[O-].[Na+]>C1COCC1.O>[C:36]([N:26]1[CH2:27][CH2:28][CH:23]([C:7]2[C:8]3[S:12][C:11]([NH:13][C:14](=[O:22])[C:15]4[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=4)=[N:10][C:9]=3[C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[CH2:24][CH2:25]1)(=[O:38])[CH3:37]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22719536N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-2-methyl-isonicotinamide hydrochloride

Product 1

HCID 10238063N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-2-methyl-isonicotinamideYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.75 g (0.165 mMol) N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-2-methyl-isonicotinamide hydrochloride (1:2) in 4 ml THF were added 0.05 ml triethyl amine. At 0° C. 0.019 ml (0.2 mMol) acetic anhydride was added dropwise and stirred for 1 h. Then a mixture of 5 ml sat. aqueous sodium bicarbonate and 10 ml water were added. A precipitation formed, which was filtered. The residue on the filter was triturated in water. Upon isolation and drying in vacuo one obtained 0.052 g (74%) N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-2-methyl-isonicotinamide as a white solid. F.p.: 213-215° C.

Workup

  1. customAt 0° C
  2. additionwere added
  3. customA precipitation
  4. customformed
  5. filtrationwhich was filtered
  6. customThe residue on the filter was triturated in water
  7. customUpon isolation and drying in vacuo one

Sources & evidence

ORD record
ord-af0c6559cfe94c979bd02125f094d2ab
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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