5-Hydroxyindoleacetic Acid → HCID 178474309, compound

HRID 1819701Notes

Reaction equation

HRID 1819701 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]([NH2:26])=[N:11][C:12](=[O:25])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23]C)[CH:21]=3)[NH:16][CH:15]=2)[CH:5]=[C:4]([Cl:27])[C:3]=1[NH:28][C:29](=[O:31])[CH3:30].OC1C=C2C(=CC=1)NC=C2CC(O)=O.C(NC1C(Cl)=CC(CN)=CC=1Cl)(=O)C>>[Cl:27][C:4]1[CH:5]=[C:6]([CH2:8][NH:9][C:10]([NH2:26])=[N:11][C:12](=[O:25])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:23])[CH:21]=3)[NH:16][CH:15]=2)[CH:7]=[C:2]([Cl:1])[C:3]=1[NH:28][C:29](=[O:31])[CH3:30]

Participants

4

Reactant 3

HCID 18265-Hydroxyindoleacetic AcidHCID 58962993N-(4-(aminomethyl)-2,6-dichlorophenyl)acetamideHCID 178488081HCID 178488081, compound

Product 1

HCID 178474309HCID 178474309, compound

Procedure

In a manner similar to that used in the preparation of the compound of example 2, but using 2-(5-hydroxy-1H-indol-3-yl)acetic acid in step 14 (A) and 4-acetamido-3,5-dichloro-benzylamine (preparation B) in step 14 (B), the title compound was prepared. MS (ESI) (M+H)+=448.05 1H-NMR (500 MHz, CD3OD) δ 7.41 (s, 2 H), 7.15-7.30 (m, 2 H), 6.93 (d, J=2.44 Hz, 1 H), 6.73 (dd, J=8.70, 2.29 Hz, 1 H), 4.47 (s, 2 H), 3.88 (s, 2 H), 2.19 (s, 3 H).

Sources & evidence

ORD record
ord-7758081ce6564169984147ba03c805f8
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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