Morpholine → (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-morpholin-4-ylmethyl-isonicotinamide

HRID 985809Notes

Reaction equation

HRID 985809 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:23][O:22][CH2:21][CH2:20][O:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>>[O:19]1[CH2:20][CH2:21][O:22][CH2:23][CH:18]1[C:17]1[C:11]2[S:10][C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:26]=[CH:27][N:28]=[C:3]([CH2:2][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[CH:4]=3)=[N:13][C:12]=2[C:14]([O:24][CH3:25])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 22507718(+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 22507728(+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-morpholin-4-ylmethyl-isonicotinamideYield 62%

Procedure

A suspension of 100 mg (0.24 mmol) (+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide, 155 mg (0.48 mmol) cesium carbonate and 0.42 ml (4.76 mmol) morpholine was ultrasonicated at room temperature for 10 min. The reaction mixture was then concentrated in vacuo. Flash chromatography (1/1 acetone/hexane) followed by trituration in ether and hexane afforded 70 mg (62%) (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-morpholin-4-ylmethyl-isonicotinamide as an off-white solid. [α]D20=+89.2° (c=0.49, CHCl3), ES-MS m/e (%): 471 (M+H+, 100).

Workup

  1. customwas ultrasonicated at room temperature for 10 min
  2. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-486d992dcede472bb6c3f46b7259961a
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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