3-Chlorobenzoic Acid → 2-(5-Carbamimidoyl-2-((3-chlorobenzamido)methyl)phenylamino)acetic acid

HRID 1296770Notes

Reaction equation

HRID 1296770 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=C(C)O[N:11]=2)=[CH:6][C:5]=1[NH:16][CH2:17][C:18]([O:20]CC1C=CC=CC=1)=[O:19].[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](O)=[O:33]>[Ni].CO>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][NH:2][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[C:29]([Cl:28])[CH:30]=2)=[C:5]([NH:16][CH2:17][C:18]([OH:20])=[O:19])[CH:6]=1)(=[NH:11])[NH2:14]

Participants

5

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 69490392Benzyl 2-(2-(aminomethyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)acetate hydrochloride

Product 1

HCID 112453552-(5-Carbamimidoyl-2-((3-chlorobenzamido)methyl)phenylamino)acetic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Compound 58d was reacted with 3-chlorobenzoic acid and subsequently hydrogenated according to the procedure described in Example 58, with the exception that Raney nickel and TEA in methanol was used for the hydrogenation step, to give Example 64. ESI-MS m/e 361.5 (M+1).

Workup

  1. customto give Example 64

Sources & evidence

ORD record
ord-7fa9b7b87950439b856262bf53d78f9c
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

Loading…