6-Fluoroindole-3-acetic acid → HCID 178474310, compound

HRID 1819703Notes

Reaction equation

HRID 1819703 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](OC)[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].[F:32]C1C=C2C(C(CC(O)=O)=CN2)=CC=1.C(NC1C(Cl)=CC(CN)=CC=1Cl)(=O)C>>[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][C:19]([F:32])=[CH:20][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]

Participants

4

Reactant 3

HCID 27745076-Fluoroindole-3-acetic acidHCID 58962993N-(4-(aminomethyl)-2,6-dichlorophenyl)acetamideHCID 178488081HCID 178488081, compound

Product 1

HCID 178474310HCID 178474310, compound

Procedure

In a manner similar to that used in the preparation of the compound of example 2, but using 2-(6-fluoro-1H-indol-3-yl)acetic acid in step 16 (A) and 4-acetamido-3,5-dichloro-benzylamine (preparation B) in step 16 (B), the title compound was prepared. MS (ESI) (M+H)+=450.08 1H-NMR(500 MHz, CD3OD) δ 7.52 (dd, J=8.55, 5.19 Hz, 1 H), 7.42 (s, 2 H), 7.28 (s, 1 H), 7.09 (dd, J=9.77, 2.14 Hz, 1 H), 6.77-6.95 (m, 1 H), 4.50 (s, 2 H), 3.95 (s, 2 H), 2.19 (s, 3 H).

Sources & evidence

ORD record
ord-2e6c6b1a26f84f2ba54542c8bba57d37
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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