4-Chlorophenylboronic acid → HCID 12043984, compound

HRID 720818Notes

Reaction equation

HRID 720818 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[NH:23][CH2:24][C:25]([OH:27])=O.Cl.Cl.N1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37]CCCN.ClC(O[C:46]1C=CC([N+]([O-])=O)=C[CH:47]=1)=O.N[CH2:56][C:57]([O:59]C(C)(C)C)=[O:58]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:36]2[CH:35]=[CH:34][C:33]([CH:32]([NH:37][C:25](=[O:27])[CH2:24][NH:23][C:22]([NH:21][CH2:20][CH2:19][CH2:18][NH:17][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=3)=[O:28])[CH2:56][C:57]([OH:59])=[O:58])=[CH:47][CH:46]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 742994-Chlorophenylboronic acidHCID 821294-Nitrophenyl chloroformateHCID 151417Glycine tert-butyl esterHCID 21895317{3-[3-(Pyridin-2-ylamino)propyl]ureido}acetic acidHCID 6973543799768-43-1

Product 1

HCID 12043984HCID 12043984, compound

Procedure

prepared by reaction of the resin AB with 4-chlorophenylboronic acid as described in Example 1, is reacted with {3-[3-(pyridin-2-ylamino)propyl]ureido}acetic acid (prepared analogously to Example 1 by reaction of N1-pyridin-2-ylpropane-1,3-diamine dihydrochloride with 4-nitrophenyl chloroformate and tert-butyl aminoacetate and cleavage of the ester) and cleaved off from the support, giving 3-(4′-chlorobiphenyl-4-yl)-3-(2-{3-[3-(pyridin-2-ylamino)propyl]ureido}ethanoylamino)propionic acid.

Sources & evidence

ORD record
ord-33d58087f30f40e48a21203db2db1f02
Source dataset
uspto-grants-2006_11
Patent number
US07135587B2

Reaction notes

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