3-Chloro-2-fluoroaniline → HCID 16046966, compound

HRID 1690693Notes

Reaction equation

HRID 1690693 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]3[CH:13]=[C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.Cl.[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([NH:37]N)[CH:32]=2)=[CH:27][C:26]=1[CH3:39].CC1C=C(B(O)O)C=CC=1[F:47].ClC1C(F)=C(C=CC=1)N>>[F:47][C:32]1[C:31]([C:28]2[CH:29]=[CH:30][C:25]([F:24])=[C:26]([CH3:39])[CH:27]=2)=[CH:36][CH:35]=[C:34]2[C:33]=1[NH:37][C:2]1[C:3]3[CH:4]=[CH:5][C:6]([C:12]4[CH:13]=[C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=4)=[CH:7][C:8]=3[CH2:9][CH2:10][C:11]2=1

Participants

5

Reactant 4

HCID 750143-Chloro-2-fluoroanilineHCID 2774580(4-Fluoro-3-methylphenyl)boronic acidHCID 57618475HCID 57618475, compoundHCID 66904603HCID 66904603, compound

Product 1

HCID 16046966HCID 16046966, compound

Procedure

The title material is prepared by reacting N-[3-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-phenyl]-methanesulfonamide and (4′-Fluoro-3′-methyl-biphenyl-3-yl)-hydrazine hydrochloride (prepared as in example 70, steps 1 and 2 except using 3-methyl-4-fluorophenylboronic acid and 3-chloro-2-fluoroaniline as the coupling partners) in an analogous manner to example 1, step 3 except that purification is accomplished by reverse phase UV triggered HPLC: 1H NMR (400 MHz, d6-DMSO) δ 12.66 (s, 1H), 9.88 (s, 1H), 8.82 (d, J=8.7 Hz, 1H), 8.31 (m, 1H), 8.29 (d, J=8.6 Hz, 1H), 8.08 (d, J=8.2 Hz, 1H), 7.94 (m, 1H), 7.80 (d, J=8.6 Hz, 1H), 7.66 (m, 1H), 7.61 (m, 2H), 7.48 (m, 1H), 7.30 (m, 2H), 3.09 (m, 2H), 3.04 (s, 3H), 2.97 (m, 2H), 2.08 (s, 3H); LC/MS calculated for [M+H]+ C30H25F2N2O2S: 515.6, found: 515.0.

Workup

  1. customprepared as in example 70, steps 1 and 2
  2. customexcept that purification

Sources & evidence

ORD record
ord-acbd724494394699923b4372090468aa
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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