Benzoic Acid → HCID 15295811, compound

HRID 865392Notes

Reaction equation

[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:22]([C:25]1[N:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[S:43](=[O:46])(=[O:45])[NH2:44])=[CH:33][CH:32]=2)[C:28]2[CH:47]=[C:48]([C:52]3[N:56]([CH3:57])[C:55]4[CH:58]=[CH:59][CH:60]=[CH:61][C:54]=4[N:53]=3)[CH:49]=[C:50]([CH3:51])[C:27]=2[N:26]=1)[CH2:23][CH3:24].N12CCCN=C1CCCCC2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(OCC)(=O)C>[CH2:22]([C:25]1[N:29]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[S:43]([NH:44][C:1](=[O:9])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)(=[O:45])=[O:46])=[CH:35][CH:36]=2)[C:28]2[CH:47]=[C:48]([C:52]3[N:56]([CH3:57])[C:55]4[CH:58]=[CH:59][CH:60]=[CH:61][C:54]=4[N:53]=3)[CH:49]=[C:50]([CH3:51])[C:27]=2[N:26]=1)[CH2:23][CH3:24]

Participants

Conditions

Temperature: 55 °C

Procedure

145 mg of benzoic acid and 192 mg of carbonyldiimidazole are stirred in 1 ml of tetrahydrofuran for 2 hours at 50° C. To this is added a solution of 163 mg of 4'-[(2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl)-methyl]-2-sulphamoyl-biphenyl, 0.133 ml of 1,8-diazabicyclo-[5.4.0]undec-7-ene and 1 ml of tetrahydrofuran and the mixture is maintained at 55° C. for 2.5 hours. Then 50 ml of ethyl acetate and 20 ml of 5% citric acid are added. The organic phase is dried with sodium sulphate and evaporated down. The residue obtained is chromatographed over silica gel with dichloromethane/ethanol (95:5).

Workup

dry with materialThe organic phase is dried with sodium sulphate
customevaporated down
customThe residue obtained
customis chromatographed over silica gel with dichloromethane/ethanol (95:5)

Sources & evidence

ORD record: ord-8d19d475967b4e5a984f4a044dec614a
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05565469

Reaction notes

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