Pyridine → HCID 22283106, compound

HRID 1062996Notes

Reaction equation

HRID 1062996 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-a0ad0e9dc8864f4b8787e33de5398650
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

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