Hydrochloric Acid → 2-(4-Amidinophenylethyl]-3-methyl-6-(2-methoxycarbonyl-2.3-dihydroindol-1-yl-carbonyl) imidazo[4.5-b]pyridine hydrochloride

HRID 50197Notes

Reaction equation

HRID 50197 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:34]([CH3:35])[C:14]3=[N:15][CH:16]=[C:17]([C:19]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:23][CH:22]4[C:30]([O:32][CH3:33])=[O:31])=[O:20])[CH:18]=[C:13]3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].[ClH:36].C(=O)([O-])[O-].[NH4+:41].[NH4+].C(OCC)(=O)C.C(O)C.N>CO>[ClH:36].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:34]([CH3:35])[C:14]3=[N:15][CH:16]=[C:17]([C:19]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:23][CH:22]4[C:30]([O:32][CH3:33])=[O:31])=[O:20])[CH:18]=[C:13]3[N:12]=2)=[CH:5][CH:4]=1)(=[NH:41])[NH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 184125122-[2-(4-Cyanophenyl)ethyl]-3-methyl-6-(2-methoxycarbonyl-2,3-dihydroindol-1-yl-carbonyl)-imidazo[4,5-b]pyridineHCID 86587043Ethyl acetate ethanol ammonia

Product 1

HCID 184123572-(4-Amidinophenylethyl]-3-methyl-6-(2-methoxycarbonyl-2.3-dihydroindol-1-yl-carbonyl) imidazo[4.5-b]pyridine hydrochlorideYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared analogously to Example 1 from 2-[2-(4-cyanophenyl)ethyl]-3-methyl-6-(2-methoxycarbonyl-2,3-dihydroindol-1-yl-carbonyl)imidazo[4,5-b]pyridine, methanolic hydrochloric acid, methanol, and ammonium carbonate. Yield: 20% of theory, C27H26N6O3 (482.54); Rf value: 0.30 (silica gel; ethyl acetate/ethanol/ammonia=50:45:5); EKA mass spectrum: (M+H)+=483.

Sources & evidence

ORD record
ord-b6e4f9dce14c45c49596fa618965b7d5
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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