HCID 86758816, compound → HCID 86758815, compound

HRID 1636011Notes

Reaction equation

HRID 1636011 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([C:22]([N:24]([CH3:41])[CH:25]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([C:38](=[NH:40])[NH2:39])=[CH:34][CH:33]=4)[C:26]([O:28]CC)=[O:27])=[O:23])=[CH:21][C:14]=3[N:13]=2)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[CH:42]([O-:44])=[O:43]>ClCCl.CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([C:22]([N:24]([CH3:41])[CH:25]([CH2:31][C:32]4[CH:33]=[CH:34][C:35]([C:38](=[NH:39])[NH2:40])=[CH:36][CH:37]=4)[C:26]([OH:28])=[O:27])=[O:23])=[CH:21][C:14]=3[N:13]=2)=[CH:6][CH:5]=1)(=[NH:2])[NH2:3].[CH:42]([O-:44])=[O:43]

Participants

3

Reactant 1

HCID 86758816HCID 86758816, compound

Product 1

HCID 86758815HCID 86758815, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The reaction takes place analogously to the procedure described in Example 30 starting from ethyl 2-{2-[2-(4-amidinophenyl)-ethyl]-1-methyl-benzimidazol-5-yl-carbonyl-(methylamino)}-3-(4-amidinophenyl)-propionate (Example 29, 1.7 mmol). The product is obtained by crystallisation from dichloromethane/methanol. Yield: >90%; melting point: 255° C.; mass: calc.: [525], found: [M+H]+ 526; 1H-NMR (250 MHz, DMSO-d6): δ [ppm]=10.20 (1H, s, COOH); 8.61 (1H, s, HCOOH); 8.09-6.77 (17H, m, 2 C(═NH)NH2, aryl-H); 5.37 (1H, m, N—CH—); 3.78 (3H, s, aryl-N—CH3); 3.33 (4H, s, aryl-CH2—CH2—); 2.98 (3H, s, CO—N—CH3).

Sources & evidence

ORD record
ord-86885917db88406096e71f293aae2cfc
Source dataset
uspto-grants-2003_01
Patent number
US06512000B1

Reaction notes

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