4-Chlorophenyl Isocyanate → HCID 178522071, compound

HRID 2415607Notes

Reaction equation

HRID 2415607 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]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([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])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine

Product 1

HCID 178522071HCID 178522071, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-(7-chloroquinolin-4-yl)-cyclohexane-1,4-diamine (20 mg, 0.07 mmol) in chloroform (0.5 mL) at 20° C. was treated with 4-chlorophenyl isocyanate (11 mg,0.07 mmol). The mixture was shaken at room temperature for 18 hours then concentrated under reduced pressure. The compound was purified by reverse phase HPLC to provide the desired compound. MS (ESI (+)) m/e 429 (M+H)+; 1H NMR (500 MHz, DMSO) δ ppm 8.55 (s, 1 H), 8.52 (d, 1 H), 8.45 (d, 1 H), 7.83 (s, 1 H), 7.57 (d, 1 H), 7.41 (d, 2 H), 7.26 (d, 2 H), 6.70 (s, 1 H), 6.31 (d, 1 H), 3.78 (s, 1 H), 3.71 (s, 1 H), 1.63-1.93 (m, 8 H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe compound was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d976414c52b948a990ead33910df6dfc
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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