4-Chlorobenzenesulfonyl chloride → HCID 178527586, compound

HRID 2415610Notes

Reaction equation

HRID 2415610 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]3[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:19][C@H:16]2[CH2:15][CH2:14][C@@H:13]([NH:12][C:6]3[C:5]4[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]=[CH:8][CH:7]=3)[CH2:18][CH2:17]2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine

Product 1

HCID 178527586HCID 178527586, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of N-(7-chloroquinolin-4-yl)-cyclohexane-1,4-diamine (20 mg, 0.07 mmol) in pyridine (1.0 mL) at 20 C was treated with 4-chlorobenzenesulfonyl chloride (15 mg, 0.07 mmol). The reaction was shaken at room temperature for 18 hours then concentrated. The crude compound was purified by reverse phase HPLC to provide the desired compound. MS (ESI (+)) m/e 450 (M+H)+; 1H NMR (500 MHz, DMSO) δ ppm 8.88 (d, 1 H), 8.71 (d, 1 H), 8.53 (d, 1 H), 7.93 (d, 1 H), 7.87 (d, 2 H), 7.81 (dd, 1 H), 7.70 (d, 3 H), 6.95 (d, 1 H), 3.86 (br.s, 1 H), 3.14 (m, 1 H), 1.89 (m, 2 H), 1.74 (m, 4 H), 1.58 (m, 2 H).

Workup

  1. concentrationthen concentrated
  2. customThe crude compound was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-7e7ef72ad3264f9a8407bb7eac0b8373
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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