Pyridine → HCID 22283106, compound

HRID 2308472Notes

Reaction equation

HRID 2308472 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1.[Cl:19][CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl>[Cl:19][CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:1][C:2]2[S:3][C:4]3[C:10]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=3[N:6]=2)=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 114028614-Methoxy-7-morpholinobenzo[d]thiazol-2-amine

Product 1

HCID 22283106HCID 22283106, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

and 2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol (1.0 g, 3.8 mmol), 4-(chloromethyl) benzoyl chloride (810 mg, 4.2 mmol) and pyridine (0.36 ml, 4.5 mmol) are reacted in dichloromethane (20 ml) for 18 h. The reaction is quenched with water (25 ml) and brought to pH 8.0 with sodium carbonate. The mixture is extracted with dichloromethane and the combined organic layers are dried and evapoarted to dryness. Flash chromatography (silica, eluent methylene chloride containing 2.5% methanol) affords the product as white crystalls in 54% yield. MS: m/e=418 (M+H+).

Workup

  1. customThe reaction is quenched with water (25 ml)
  2. extractionThe mixture is extracted with dichloromethane
  3. customthe combined organic layers are dried
  4. customFlash chromatography (silica, eluent methylene chloride containing 2.5% methanol) affords the product as white crystalls in 54% yield

Sources & evidence

ORD record
ord-c85d075a6f7343f9879db0752736a12a
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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