Hydrochloric Acid → HCID 58954865, compound

HRID 333257Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:16].Cl>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][NH2:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:16]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68674106HCID 68674106, compound

Product 1

HCID 58954865HCID 58954865, compoundYield 19%

Procedure

The title compound was synthesized from 1-(4-chloro-3-fluorophenyl)-cyclohexanecarbonitrile using General Procedure E and was obtained in 19% yield as a clear oil. HPLC Rt=8.28 min. LCMS Rt=8.13 min, m/z=242 (M+1). HCl salt −1H NMR (DMSO-d6, δ): 7.35 (t, J=8.1 Hz, 1H), 7.17 (d, J=11.3 Hz, 1H), 7.10 (d, J=8.4 Hz, 1H), 2.82 (s, 2H), 2.1 (m, 2H), 1.7-1.1 (m, 8H). 13C NMR (DMSO-d6, δ, mult): 159.2(0), 156.7(0), 143.1(0), 143.0(0), 130.6(1), 124.1(1), 124.1(1), 118.5(0), 118.3(0), 116.2(1), 116.0(1), 50.2(2), 40.6(0), 33.3(2), 25.5(2), 21.4(2).

Workup

customwas obtained in 19% yield as a clear oil

Sources & evidence

ORD record: ord-b951f88670064dbd979d3bf7553662ba
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Reaction notes

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