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

HRID 43569Notes

Reaction equation

HRID 43569 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:15]3[N:16]([C:20]([O:22]C(C)(C)C)=O)[CH2:17][CH2:18][O:19][C:14]=3[CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.C(OCC)(=O)C.[C:36]([O:43][CH2:44][CH3:45])(=[O:42])[CH2:37][CH2:38]C([O-])=O.CCN=C=NCCCN(C)C.Cl.C(N(CC)C(C)C)(C)C>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:15]3[N:16]([C:20](=[O:22])[CH2:38][CH2:37][C:36]([O:43][CH2:44][CH3:45])=[O:42])[CH2:17][CH2:18][O:19][C:14]=3[CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 17119674-Ethoxy-4-oxobutanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21866389Hydrogen chloride-ethyl acetateHCID 67548869HCID 67548869, compound

Product 1

HCID 67549783Ethyl 4-(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-4-oxobutanoateYield 38.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The same operation as in Example (93a) was performed using tert-butyl 7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate obtained in Example (95c) (0.11 g, 0.27 mmol), a 4 N hydrochloric acid/ethyl acetate solution (8 ml, 32 mmol), monoethyl succinate (150 mg, 1 mmol), WSC hydrochloride (288 mg, 1.5 mmol), N,N-diisopropylethylamine (0.52 g, 4 mmol) and DMAP (10 mg). Purification by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1, 2/1, 2/3, 0/1) gave 45 mg of the title compound as a light yellow solid (38%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1, 2/1, 2/3, 0/1)

Sources & evidence

ORD record
ord-b329bccfa4f845fe82922597a6f5b049
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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