Hydrochloric Acid → 2-Chloro-4-{4-[4-(diethylamino)cyclohexylamino]-3-(methylsulfonyl)quinolin-6-yl}-6-methoxyphenol dihydrochloride

HRID 2271769Notes

Reaction equation

HRID 2271769 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:16][CH:17]1[CH2:22][CH2:21][CH:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:19][CH2:18]1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([O:44][CH3:45])[C:30]=1[OH:46].[ClH:47]>>[ClH:28].[ClH:47].[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]3[NH:16][CH:17]2[CH2:22][CH2:21][CH:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:19][CH2:18]2)[CH:32]=[C:31]([O:44][CH3:45])[C:30]=1[OH:46]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 177502302-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 68092001N1-[6-Bromo-3-(methylsulfonyl)quinolin-4-yl]-N4,N4-diethylcyclohexane-1,4-diamine

Product 1

HCID 667159792-Chloro-4-{4-[4-(diethylamino)cyclohexylamino]-3-(methylsulfonyl)quinolin-6-yl}-6-methoxyphenol dihydrochlorideYield 50%

Procedure

Following general procedure D, N1-[6-bromo-3-(methylsulfonyl)quinolin-4-yl]-N4,N4-diethylcyclohexane-1,4-diamine (40 mg, 0.088 mmol) was reacted with 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (50 mg, 0.176 mmol) to afford, after treatment with 1M HCl, the desired product (24.5 mg, 50%) as an orange-brown solid: 1H NMR (500 MHz, DMSO-d6+D2O) δ 8.91 (d, J=8.0 Hz, 1H), 8.44-8.32 (m, 2H), 8.08 (d, J=8.5 Hz, 1H), 7.48-7.27 (m, 2H), 3.98-3.95 (m, 3H), 3.46 (d, J=11.4 Hz, 5H), 3.28-3.03 (m, 5H), 2.38 (s, 2H), 2.27 (d, J=13.0 Hz, 1H), 2.15 (s, 1H), 2.10-1.96 (m, 2H), 1.90-1.69 (m, 3H), 1.33-1.23 (m, 6H); ESI MS m/z 532 [C27H34ClN3O4S+H]+; HPLC 98.9% (AUC), tR=10.49 min.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-05a40fe1dbbf45b59322dc0de8ceb1d3
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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