Diisopropylethylamine → 1-{1-[3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylethyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2101965Notes

Reaction equation

HRID 2101965 reaction equation
[C:1]([C:3]1[C:4]([C:19]([F:22])([F:21])[F:20])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)[C:7]([CH3:18])=[CH:6]2)#[N:2].[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[NH:33])[NH:31]O)=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>CC#N>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:33]=[C:13]([C:12]([N:8]3[C:9]4[C:5](=[C:4]([C:19]([F:21])([F:22])[F:20])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=4)[CH:6]=[C:7]3[CH3:18])([CH3:17])[CH3:16])[O:15][N:31]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578005042-[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]-2-methylpropanoic acidHCID 178513323HCID 178513323, compound

Product 1

HCID 578003111-{1-[3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylethyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized as described in Example 37 from 2-[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]-2-methylpropanoic acid and 4-fluoro-N-hydroxybenzenecarboximidamide using MeCN as the solvent, and HATU (1.05 eq), DIEA (1.05 eq), instead of EDCl, for the first coupling step: MS (ES) m/z 429 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-61060d12252f4162b4f490cc99afa648
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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