3-Aminobenzamide → HCID 178500658, compound

HRID 1713744Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[C:11](N1C=CN=C1)(N1C=CN=C1)=S.[NH:23]([C:25](=[O:46])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([C@H:35]2[CH2:40][CH2:39][C@H:38]([CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH2:37][CH2:36]2)=[CH:31][CH:30]=1)=[O:27])[NH2:24].C1N=CN(C(N2C=NC=C2)=O)C=1>CC#N.CN(C=O)C>[NH2:7][C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:11]2[O:46][C:25]([C:26]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([C@H:35]4[CH2:36][CH2:37][C@H:38]([CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH2:39][CH2:40]4)=[CH:33][CH:34]=3)=[O:27])=[N:23][N:24]=2)[CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Aminobenzamide (54 mg, 0.39 mmol) was added to a solution of thiocarbonyldiimidazole (71 mg, 0.39 mmol) in CH3CN (5 mL) and the mixture was stirred for 16 h. Methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclohexyl]acetate (Intermediate 43) (110 mg, 0.33 mmol) and DMF (5 mL) was added and the mixture was stirred at 50° C. until a clear solution was obtained. PS-CDI (527 mg) was added and the temperature raised to 80° C. for 16 h. The mixture was filtered whilst hot and the polymer washed with DMF (2×5 mL). The filtrates were concentrated by evaporation to give the title compound as a solid; MS m/e (M+Na)+ 500; HPLC retention time=2.26 minutes.

Workup

stirringthe mixture was stirred at 50° C. until a clear solution
customwas obtained
filtrationThe mixture was filtered whilst hot and the polymer
washwashed with DMF (2×5 mL)
concentrationThe filtrates were concentrated by evaporation

Sources & evidence

ORD record: ord-b782d87ddbb94208b871bf91905fd0a9
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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