4-Fluorophenylacetyl chloride → HCID 178520284, compound

HRID 2415613Notes

Reaction equation

HRID 2415613 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.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](Cl)=[O:29])=[CH:23][CH:22]=1>ClCCl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@@H:13]3[CH2:14][CH2:15][C@H:16]([NH:19][C:28](=[O:29])[CH2:27][C:24]4[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=4)[CH2:17][CH2:18]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 37449884-Fluorophenylacetyl chlorideHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine

Product 1

HCID 178520284HCID 178520284, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of N-(7-chloroquinolin-4-yl)-cyclohexane-1,4-diamine (20 mg, 0.07 mmol) in dichloromethane (1.0 mL) and triethylamine (0.01 mL) at 20° C. was treated with (4-fluoro-phenyl)-acetyl chloride (12 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 412 (M+H)+; 1H NMR (500 MHz, DMSO) δ ppm 8.87 (d, 1 H), 8.74 (d, 1 H), 8.54 (d, 1 H), 8.01 (d, 1 H), 7.95 (m, 1 H), 7.80 (dd, 1 H), 7.31 (m, 2 H), 7.12 (m, 2 H), 6.97 (d, 1 H), 3.91 (br.s, 1 H), 3.80 (br.s, 1 H), 3.47 (s, 2 H), 1.57-1.98 (m, 8 H).

Workup

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

Sources & evidence

ORD record
ord-5d2dc1b966254cd7b046a03fac917706
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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