Thionyl Chloride → Ethyl 2-[(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

HRID 43607Notes

Reaction equation

HRID 43607 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:38]=[CH:37][C:20]2[N:21]([CH2:25][C:26]3[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=3[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:22][CH2:23][O:24][C:19]=2[CH:18]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][C:17]2[CH:38]=[CH:37][C:20]3[N:21]([CH2:25][C:26]4[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=4[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:22][CH2:23][O:24][C:19]=3[CH:18]=2)=[O:11])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 67549293Ethyl 2-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

Product 1

HCID 67548775Ethyl 2-[(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateYield 77.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.14 g, 0.8 mmol), thionyl chloride (3 mL), ethyl 2-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate obtained in Example (104b) (0.35 g, 1.12 mmol) and pyridine (5 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1) to obtain 0.29 g of the title compound as a yellow solid (77%).

Workup

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1)

Sources & evidence

ORD record
ord-3c2ba38416284b0c8c508b387e2d31d6
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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