2-Chlorobenzaldehyde → HCID 10370763, compound

HRID 984454Notes

Reaction equation

HRID 984454 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[SH:9].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1S.Cl[C:19]1C=CC=C[C:20]=1[CH:21]=[O:22].ClC1C=C(C=CC=1F)C=O.NCCCCCCO.[O:45]=[C:46]1[N:50]([CH:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)[C:49]2[CH:57]=[CH:58][CH:59]=[CH:60][C:48]=2[NH:47]1>>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:9][C:3]1[CH:4]=[CH:5][C:6](/[CH:19]=[CH:20]/[C:21]([N:54]2[CH2:53][CH2:52][CH:51]([N:50]3[C:49]4[CH:57]=[CH:58][CH:59]=[CH:60][C:48]=4[NH:47][C:46]3=[O:45])[CH2:56][CH2:55]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

7

Reactant 6

HCID 69962-ChlorobenzaldehydeHCID 199606-Amino-1-hexanolHCID 707302,4-DichlorobenzenethiolHCID 805982-BromobenzenethiolHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 5938663-Chloro-4-fluorobenzaldehyde

Product 1

HCID 10370763HCID 10370763, compound

Procedure

The title compound was prepared by the procedures described in Example 1 substituting 2,4-dichlorothiophenol with 2-bromothiophenol, 2-chlorobenzaldehyde with 3-chloro-4-fluoro-benzaldehyde, and 6-amino-1-hexanol with 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine. 1H NMR (DMSO-d6, 300 MHz) δ 8.14 (d, J=1.5 Hz, 1H), 7.80 (dd, J=7.9, 1.3 Hz, 1H), 7.67 (dd, J=8.1, 1.8 Hz, 1H), 7.48 (ap s, 2H), 7.44 (dt, J=7.5, 1.2, 1H), 7.34 (dt, J=7.6, 1.6, 1H), 7.26 (dd, J=7.7, 1.8 Hz, 1H), 7.22 (m, 1H), 7.06 (d, J=8.1, 1H), 6.97 (ap d, J=2.6, 3H), 4.64 (m, 1H), 4.48 (m, 2H), 2.79 (m, 2H), 2.29 (m, 2H), 1.78 (in, 2H). HRMS calculated for C27H23N3O2S1Br1Cl1: 568.0461. Observed: 568.0477.

Sources & evidence

ORD record
ord-8e1659d0933b4156aaf7ee2c3c49d1df
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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