5-Bromo-3-indoleacetic acid → n-(4-{n'-[2-(5-Bromo-1h-indol-3-yl)-acetyl]-guanidinomethyl}-2,6-dichloro-phenyl)-acetamide

HRID 1819706Notes

Reaction equation

HRID 1819706 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][C:12]([N:14]=[C:15]([NH2:30])[NH:16][CH2:17][C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([NH:25][C:26](=[O:28])[CH3:27])=[C:20]([Cl:29])[CH:19]=3)=[O:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Br:31]C1C=C2C(=CC=1)NC=C2CC(O)=O>>[Br:31][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:2]=1)[NH:8][CH:7]=[C:6]2[CH2:11][C:12]([N:14]=[C:15]([NH2:30])[NH:16][CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([NH:25][C:26](=[O:28])[CH3:27])=[C:20]([Cl:29])[CH:19]=1)=[O:13]

Participants

3

Reactant 2

HCID 967345-Bromo-3-indoleacetic acidHCID 178474305HCID 178474305, compound

Product 1

HCID 178474306n-(4-{n'-[2-(5-Bromo-1h-indol-3-yl)-acetyl]-guanidinomethyl}-2,6-dichloro-phenyl)-acetamide

Procedure

In a manner similar to that used in the preparation of the compound of example 1, but using 2-(5-bromo-1H-indol-3-yl)acetic acid in step 20 (A), the title compound was prepared. MS (ESI) (M+H)+=509.84/511.92/513.90 1H-NMR (500 MHz, CD3OD) δ 7.73 (d, J=1.53 Hz, 1 H), 7.46 (s, 2 H), 7.29-7.40 (m, 2 H), 7.26 (d, J=1.83 Hz, 1 H), 4.54 (s, 2 H), 3.96 (s, 2 H), 2.19 (s, 3 H).

Sources & evidence

ORD record
ord-bf3395e47db24ff3a0b0f2777d7366ed
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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