4-Fluoro-3-(trifluoromethyl)aniline → HCID 178495284, compound

HRID 69786Notes

Reaction equation

HRID 69786 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[C:8]([NH:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])=[N:7][O:6][N:5]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[C:24]([F:27])([F:26])[F:25]>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:3]([C:4]2[C:8]([NH:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])=[N:7][O:6][N:5]=2)=[N:2][OH:1])=[CH:19][C:18]=1[C:24]([F:25])([F:26])[F:27]

Participants

3

Reactant 2

HCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 136330170HCID 136330170, compound

Product 1

HCID 178495284HCID 178495284, compoundYield 87%

Procedure

The desired compound was prepared according to the procedure of Example 1, step F, using N-hydroxy-4-[(3-methoxypropyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride and 4-fluoro-3-(trifluoromethyl)benzeneamine as the starting materials in 87% yield. LCMS for C14H16F4N5O3 (M+H)+: m/z=378.1. 1H NMR (400 MHz, DMSO-d6): δ 11.5 (s, 1 H), 9.05 (s, 1 H), 7.30 (dd, J=10.0, 9.6 Hz, 1 H), 7.13-7.11 (m, 1 H), 7.05-7.00 (m, 1 H), 6.22 (t, J=5.7 Hz, 1 H), 3.35-3.32 (m, 2 H), 3.25-3.19 (m, 5 H), 1.79-1.72 (m, 2 H).

Sources & evidence

ORD record
ord-ce7667ec0aa74d669343b472f55ca20a
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Reaction notes

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