Potassium Hydroxide → 1-cyclohexyl-2-[2-(3-oxo-4H-1,4-benzoxazin-6-yl)-6-quinolyl]benzimidazole-5-carboxylic acid

HRID 1788514Notes

Reaction equation

HRID 1788514 reaction equation
BrC1C=CC(O)=C([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[N:22]([CH:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[C:21]5[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=5[N:19]=4)[CH:14]=3)[N:9]=2)C=1.C([C:40]1[CH:41]=[CH:42][C:43]2[O:48][CH2:47][C:46](=[O:49])[NH:45][C:44]=2[CH:50]=1)(=O)C.[OH-].[K+]>C(O)C>[CH:23]1([N:22]2[C:21]3[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=3[N:19]=[C:18]2[C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([C:40]2[CH:41]=[CH:42][C:43]4[O:48][CH2:47][C:46](=[O:49])[NH:45][C:44]=4[CH:50]=2)[CH:17]=[CH:16]3)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 36419566-Acetyl-2H-1,4-benzoxazin-3(4H)-oneHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 52760841-cyclohexyl-2-[2-(3-oxo-4H-1,4-benzoxazin-6-yl)-6-quinolyl]benzimidazole-5-carboxylic acidYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 6-acetyl-4H-benzo[1,4]oxazin-3-one (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (11 mg, 8% yield).

Sources & evidence

ORD record
ord-ae0e10489fd54c2eb3daf138afefde83
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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