{2-[4-(4-Aminobutyl)phenoxy]ethyl}carbamic acid tert-butyl ester → 4-[4-(2-Aminoethyloxy) phenyl)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride

HRID 25143Notes

Reaction equation

HRID 25143 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])=[CH:14][CH:13]=1)=O)(C)(C)C.C([NH:27][C:28]([NH:30][C:31]([C:33]1[C:38]([NH2:39])=[N:37][C:36]([NH2:40])=[C:35]([Cl:41])[N:34]=1)=[O:32])=N)CCC>>[ClH:41].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:28]([NH:30][C:31]([C:33]2[C:38]([NH2:39])=[N:37][C:36]([NH2:40])=[C:35]([Cl:41])[N:34]=2)=[O:32])=[NH:27])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 22566154{2-[4-(4-Aminobutyl)phenoxy]ethyl}carbamic acid tert-butyl esterHCID 178449224HCID 178449224, compound

Product 1

HCID 1784793394-[4-(2-Aminoethyloxy) phenyl)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride

Procedure

Using general procedure Z, 4-[4-(2{t-butoxycarbonylamino}ethyloxy)phenyl]butylamine was converted into 4-[4-(2-{t-butoxycarbonylamino}ethyloxy)phenyl)]butylamidino-3,5-diamino-6-chloropyrazinecarboxamide, m.p. 118° C., APCI MS M/Z=521[C23H33ClN8O4+H]+, which was hydrolyzed and acidified with HCL to give 4-[4-(2-aminoethyloxy)pheny)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride, m.p. >178° C. (dec), M/Z=421 [C18H25ClN8O2].

Sources & evidence

ORD record
ord-4a988aa6d0a0435cbc4fc4c1afd5ecdf
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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