Dimethylcarbamoyl Chloride → HCID 59369628, compound

HRID 1625425Notes

Reaction equation

HRID 1625425 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([CH:10]([CH3:12])[CH3:11])=[CH:5][C:4]=1[C:13]([N:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[CH:21]=2)[CH2:16]1)=[O:14].[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34]>N1C=CC=CC=1>[CH3:31][N:32]([CH3:36])[C:33]([O:2][C:3]1[C:4]([C:13]([N:15]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH:21]=3)[CH2:16]2)=[O:14])=[CH:5][C:6]([CH:10]([CH3:11])[CH3:12])=[C:7]([O:9][C:13](=[O:14])[N:15]([CH3:23])[CH3:16])[CH:8]=1)=[O:34]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 68620785HCID 68620785, compound

Product 1

HCID 59369628HCID 59369628, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (2,4-dihydroxy-5-isopropyl-phenyl)-[5-(4-methyl-piperazin-1-yl)-1,3-dihydro-isoindol-2-yl]-methanone hydrochloride salt (100 mg) and dimethylcarbamyl chloride (420 μl; 20 equivalents) in pyridine (1 ml) was heated at 140° C. for 20 minutes in a CEM discover microwave synthesiser then evaporated and re-evaporated with toluene (×3). The crude material was purified by preparative LC/MS and 55 mg of the title compound were isolated as a brown solid (formate salt). 1H NMR (400 MHz, DMSO-d6): 8.15 (1H, s), 7.42 (1H, d), 7.25-7.10 (1H, m), 7.05-6.85 (3H, m), 4.70 (2H, d), 4.54 (2H, d), 3.20-3.10 (4H, m), 3.09 (3H, s), 3.08-3.00 (1H, m), 2.95 (3H, s), 2.88 (3H, s), 2.79 (3H, s) 2.65-2.47 (4H, m), 2.35 (3H, d), 1.20 (6H, d). MS: [M+H]+ 538.

Workup

  1. customthen evaporated
  2. customre-evaporated with toluene (×3)
  3. customThe crude material was purified by preparative LC/MS

Sources & evidence

ORD record
ord-f70cc14895c5474c8ded0fd24a47cfc9
Source dataset
uspto-grants-2014_07
Patent number
US08779132B2

Reaction notes

Loading…