Dimethylcarbamoyl Chloride → HCID 90418434, compound

HRID 528005Notes

Reaction equation

HRID 528005 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)[N:8]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:4]=2[N:5]=[CH:6][N:7]=1.C(N(C(C)C)CC)(C)C.[CH3:35][N:36]([CH3:40])[C:37](Cl)=[O:38]>ClCCl>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([C:37]([N:36]([CH3:40])[CH3:35])=[O:38])[CH2:15][CH:16]=3)[N:8]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:18])=[O:19])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 90418595HCID 90418595, compound

Product 1

HCID 90418434HCID 90418434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of Example 75B (4.25 g, 10.33 mmol) and diisopropylethylamine (5.41 ml, 31.0 mmol) in 120 mL dichloromethane was added dimethylcarbamic chloride (1.333 g, 12.40 mmol). The mixture was stirred at 15° C. for 5 hours. The reaction was concentrated in vacuo, and the crude material was purified via flash chromatography: Analogix Intelliflash™ 280, 80 g silica column, 1:1 hexane/ethyl acetate to give the title compound. LC-MS (ESI+) m/z 446.0 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude material was purified via flash chromatography

Sources & evidence

ORD record
ord-3919740cce2f40fd90331d0535580705
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

Loading…