Diisopropylethylamine → 6-{2-[4-(4-methoxy-benzothiazole-2-carbonyl)-piperidin-1-yl]-acetyl}-4H-benzo[1,4]thiazin-3-one

HRID 1012944Notes

Reaction equation

HRID 1012944 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[CH2:21][C:22]([C:24]1[CH:25]=[CH:26][C:27]2[S:32][CH2:31][C:30](=[O:33])[NH:29][C:28]=2[CH:34]=1)=[O:23].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:21][C:22]([C:24]4[CH:25]=[CH:26][C:27]5[S:32][CH2:31][C:30](=[O:33])[NH:29][C:28]=5[CH:34]=4)=[O:23])[CH2:16][CH2:15]3)=[O:13])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 162180756-(Chloroacetyl)-2H-1,4-benzothiazin-3(4H)-oneHCID 67315952(4-Methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone

Product 1

HCID 119990456-{2-[4-(4-methoxy-benzothiazole-2-carbonyl)-piperidin-1-yl]-acetyl}-4H-benzo[1,4]thiazin-3-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4-methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone (83 mg, 0.3 mmol) and 6-(2-chloro-acetyl)-4H-benzo[1,4]thiazin-3-one (72.5 mg, 0.3 mmol, prepared as described in WO 02/096907) in DMF (1 ml) was treated with DIPEA (50 μl, 0.3 mmol) and the mixture was stirred at RT overnight. The mixture was poured on water and extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated. Crystallisation from ether and MeOH gave 65 mg (45%) of title compound as a beige solid.

Workup

  1. additionThe mixture was poured on water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customCrystallisation from ether and MeOH

Sources & evidence

ORD record
ord-ab8952856c8947cda8cc1dde28f28e23
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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