Dimethyl Sulfoxide → HCID 76611310, compound

HRID 2077573Notes

Reaction equation

HRID 2077573 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.C([N:24]([CH:27]([CH3:29])[CH3:28])[CH2:25][CH3:26])(C)C.CS(C)=O>O>[C:9]1([CH3:10])[CH:8]=[CH:6][CH:5]=[CH:4][C:29]=1[CH:27]1[CH2:28][CH2:26][CH2:25][N:24]1[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 51357685N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 76611310HCID 76611310, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.100 g, 0.3 mmol), 2-O— tolylpyrrolidine (0.053 g, 0.33 mmol) oxalate, diisopropylethylamine (0.20 ml, 1.2 mmol) in DMSO (1.0 g, 11 mmol) was heated under CEM microwave at 140° C., 130 W (Powermax® off) for 20 min. The resultant was diluted with 5 ml of water and filtered. The solid was dried to give a brown solid (0.065 g, 46%). MS (ESI pos. ion) Found m/z: 430, (M+H)+.

Workup

  1. filtrationfiltered
  2. customThe solid was dried

Sources & evidence

ORD record
ord-7bedb845afe643b29a5dedb0cd92f831
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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