4-Fluoroaniline → Dimethylformamide

HRID 2183372Notes

Reaction equation

HRID 2183372 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1CCCC[O:13]1)[N:7]=[C:6]2[C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](O)=[O:22])#[N:2].[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.[CH:35]1C=CC2N(O)[N:42]=[N:41]C=2C=1.CCN=C=NC[CH2:51][CH2:52][N:53]([CH3:55])[CH3:54].Cl>C1COCC1>[CH3:55][N:53]([CH2:52][C:51]1[N:2]=[C:1]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][N:7]=[C:6]3[C:18]2[CH:19]=[C:20]([C:21]([NH:32][C:31]3[CH:33]=[CH:34][C:28]([F:27])=[CH:29][CH:30]=3)=[O:22])[CH:24]=[CH:25][CH:26]=2)[NH:42][N:41]=1)[CH3:54].[CH3:9][N:8]([CH:12]=[O:13])[CH3:35]

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22480305HCID 22480305, compound

Product 2

HCID 6228DimethylformamideYield 1,072.3%HCID 178483337HCID 178483337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure of Example 367 A using the following amounts of reagents: 3-(5-cyano-1-perhydro-2H-pyran-2-yl-1H-indazol-3-yl)benzoic acid (2.65 g, 7.63 mmol), 4-fluoroaniline (2.20 mL, 23.22 mmol), HOBT (3.1 g, 22.95 mmol), EDAC.HCl (4.4 g, 22.95 mmol), anhydrous THF (50.0 mL) and anhydrous DMF (15.0 mL) (2.99 g, 89% yield) as a yellow solid. ES-MS (m/z) 441 [M+H]+.

Sources & evidence

ORD record
ord-cb640adc7b634af6ad8ce943c7a18a6e
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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