1H-Indole-3-propanoic acid → HCID 11690989, compound

HRID 1676071Notes

Reaction equation

HRID 1676071 reaction equation
NC1C=CC2N=CN(C(C3C=CC=CC=3)CC(OCC)=O)C=2C=1.N1C2C(=CC=CC=2)C(CCC(O)=O)=C1.[NH:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]([CH2:47][CH2:48][C:49]([NH:51][C:52]2[CH:53]=[CH:54][C:55]3[N:59]=[CH:58][N:57]([CH:60]([C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)[CH2:61][C:62]([O:64]CC)=[O:63])[C:56]=3[CH:73]=2)=[O:50])=[CH:39]1.[OH-].[Na+]>>[NH:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]([CH2:47][CH2:48][C:49]([NH:51][C:52]2[CH:53]=[CH:54][C:55]3[N:59]=[CH:58][N:57]([CH:60]([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)[CH2:61][C:62]([OH:64])=[O:63])[C:56]=3[CH:73]=2)=[O:50])=[CH:39]1

Participants

5

Reactant 4

HCID 37441H-Indole-3-propanoic acidHCID 14798Sodium HydroxideHCID 67351765ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoateHCID 67352635HCID 67352635, compound

Product 1

HCID 11690989HCID 11690989, compound

Procedure

Using a similar procedure to that described in Preparation 21, the title compound (25 mg) was prepared from ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate and 3-indolepropionic acid. Hydrolysis of the intermediate ethyl 3-(6-{[3-(1H-indol-3-yl)propanoyl]amino}-1H-benzimidazol-1-yl)-3-phenylpropanoate in this case was carried out using an aqueous solution of sodium hydroxide (2N), followed by RP-HPLC purification of the concentrated residue. [LCMS (Method A, Mobile Phase I) RT=4.29 min, MH+ 453].

Workup

  1. customthat described in Preparation 21
  2. customfollowed by RP-HPLC purification of the concentrated residue

Sources & evidence

ORD record
ord-d36e5dfe75674de5a8b1fda2e6ad8a34
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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