2-Chlorobenzaldehyde → HCID 86601532, compound

HRID 1815472Notes

Reaction equation

HRID 1815472 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.[CH2:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:48][CH2:47][NH:46]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:46]2[CH2:47][CH2:48][CH:49]3[C:54](=[CH:53][CH:52]=[CH:51][CH2:50]3)[CH2:45]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

7

Reactant 6

HCID 69962-ChlorobenzaldehydeHCID 70461,2,3,4-TetrahydroisoquinolineHCID 199606-Amino-1-hexanolHCID 707302,4-DichlorobenzenethiolHCID 805982-BromobenzenethiolHCID 5938663-Chloro-4-fluorobenzaldehyde

Product 1

HCID 86601532HCID 86601532, 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 tetrahydroisoquinoline. 1H NMR (DMSO-d6, 300 MHz) δ 8.12 (d, J=7.4 Hz, 1H), 7.81 (dd, J=7.7, 1.1 Hz, 1H), 7.67 (dd, J=8.3, 1.3 Hz, 1H), 7.47 (m, 2H), 7.43 (dd, J=7.5, 1.3 Hz, 2H), 7.34 (dt, J=7.6, 1.7 Hz, 1H), 7.27 (d 7.7 Hz, 1H), 7.19 (m, 4H), 7.05 (d, J=8.1 Hz, 1H), 4.92 (s, 1H), 4.72 (s, 1H), 3.95 (t, J=5.9 Hz, 1H), 3.78 (t, J=5.7 Hz, 1H), 2.89 (t, J=5.3 Hz, 1H), 2.83 (t, J=3.7, 1H). HRMS calculated for C24H19N1O2S1Br1Cl1: 484.0138. Observed: 484.0128.

Sources & evidence

ORD record
ord-fcc937dd2f314d21b6c569b443f64fe3
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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