4-Fluoroaniline → Dimethylformamide

HRID 1349874Notes

Reaction equation

HRID 1349874 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[N:7]=[C:6]2[C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=O)#N.[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.C1C=CC2N([OH:44])N=[N:41][C:39]=2C=1.CCN=C=NCC[CH2:52][N:53]([CH3:55])[CH3:54].Cl>C1COCC1>[C:39]([CH:15]1[CH2:14][O:13][CH:12]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[CH:11][CH:10]=3)[C:6]([C:18]3[CH:19]=[C:20]([C:21]([NH:32][C:31]4[CH:33]=[CH:34][C:28]([F:27])=[CH:29][CH:30]=4)=[O:23])[CH:24]=[CH:25][CH:26]=3)=[N:7]2)[CH2:17][CH2:16]1)#[N:41].[CH3:55][N:53]([CH:52]=[O:44])[CH3:54]

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 536.1%HCID 131726357HCID 131726357, 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-26142eddc52c4841a3d033d24ac5ca6f
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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