1-Chloro-4-(isocyanatomethyl)benzene → HCID 11598228, compound

HRID 1626186Notes

Reaction equation

HRID 1626186 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:23])[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:5][CH:4]=[N:3]1.[Cl:24][C:25]1[CH:34]=[CH:33][C:28]([CH2:29][N:30]=[C:31]=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][NH:30][C:31]([NH:23][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:7]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)[CH:8]=2)=[O:32])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 33723791-Chloro-4-(isocyanatomethyl)benzeneHCID 58964303HCID 58964303, compound

Product 1

HCID 11598228HCID 11598228, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(1-methyl-1H-pyrazol-5-yl)-4-(3-morpholinopropoxy)benzenamine (0.025 g, 0.079 mmol) in CH2Cl2 (0.6 mL) was treated with 4-chlorobenzyl isocyanate (0.012 mL, 0.083 mmol). The reaction was stirred for 1 h, and concentrated and purified by RP-HPLC. Lyophilization afforded a TFA salt as a white solid (0.037 g, 78%). LCMS m/z (%)=484 (M+H35Cl, 100), 486 (M+H37Cl, 38). 1H NMR (400 MHz, DMSO-d6) δ: 9.60 (s, 1H), 8.63 (s, 1H), 7.46 (d, J=1.8 Hz, 1H), 7.43 (dd, J=2.6, 8.9 Hz, 1H), 7.40-7.29 (m, 4H), 7.07 (d, J=9.0 Hz, 1H), 6.75-6.70 (m, 1H), 6.25 (d, J=1.8 Hz, 1H), 4.26 (d, J=5.8 Hz, 2H), 4.02-3.90 (m, 4H), 3.65 (s, 3H), 3.58 (t, J=12.0 Hz, 2H), 3.34 (d, J=12.4 Hz, 2H), 3.09-2.92 (m, 4H), 2.06-1.97 (m, 2H).

Workup

  1. concentrationconcentrated
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-5e6b87a1b1254e31b442881c6ac654e0
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

Loading…