Methanol → HCID 59615442, compound

HRID 43589Notes

Reaction equation

HRID 43589 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:32]=[CH:31][C:15]3[N:16]([CH2:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([O:26]C)=[O:25])[CH2:17][CH2:18][O:19][C:14]=3[CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+].CO>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:32]=[CH:31][C:15]3[N:16]([CH2:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([OH:26])=[O:25])[CH2:17][CH2:18][O:19][C:14]=3[CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67549156Methyl 3-[(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

Product 1

HCID 59615442HCID 59615442, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The same operation as in Example (91d) was performed using methyl 3-[(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate obtained in Example (100c) (0.16 g, 0.35 mmol), 2 N lithium hydroxide (3 mL, 6 mmol), methanol (3 mL) and tetrahydrofuran (8 mL), to obtain 0.11 g of the title compound as a light pink solid (71%).

Sources & evidence

ORD record
ord-7e272566924448c8adcc433027442eed
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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