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

HRID 1012943Notes

Reaction equation

HRID 1012943 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[O: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[O: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 27644586-(2-chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 67315952(4-Methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone

Product 1

HCID 119990446-{2-[4-(4-methoxy-benzothiazole-2-carbonyl)-piperidin-1-yl]-acetyl}-4H-benzo[1,4]oxazin-3-oneYield 81%

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]oxazin-3-one (68 mg, 0.3 mmol) 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 gave 113 mg (81%) 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

Sources & evidence

ORD record
ord-cb3657fb8ec946a0affb41ff77739e51
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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