Acetic Acid → [4-({[3-(8-Methyl-3-phenylcinnolin-4-yl)phenyl]amino}methyl)phenyl]acetic acid

HRID 643296Notes

Reaction equation

C[O:2][C:3](=[O:36])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[C:28]4[C:23](=[C:24]([CH3:29])[CH:25]=[CH:26][CH:27]=4)[N:22]=[N:21][C:20]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:14]=2)=[CH:7][CH:6]=1.O.[OH-].[Li+].C(O)(=O)C>C1COCC1.CO.O>[CH3:29][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[N:22]=[N:21][C:20]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[C:19]2[C:15]1[CH:14]=[C:13]([NH:12][CH2:11][C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:36])=[O:2])=[CH:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of (4-{[3-(8-methyl-3-phenyl-cinnolin-4-yl)-phenylamino]-methyl}-phenyl)-acetic acid methyl ester in THF/methanol/water (2:1:1, 10 mL) was added lithium hydroxide monohydrate (0.1 g). The reaction was stirred at 40° C. for 1 hour. The reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and dried over P2O5 to give the title compound as an orange solid (0.02 g, 43% for Step 5 and Step 6). MS (ESI) m/z 460; HRMS (ESI, [M+H]+) 460.2012.

Workup

customthe solid was collected
dry with materialdried over P2O5

Sources & evidence

ORD record: ord-9c57935b3a274c209ffd398cdf61191f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700595B2

Reaction notes

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