Diisopropylethylamine → HCID 86670690, compound

HRID 877981Notes

Reaction equation

HRID 877981 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:21])[C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:9]([NH:19][CH3:20])=[CH:8][N:7]=1.CCN(C(C)C)C(C)C.[F:31][C:32]([F:47])([F:46])[C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[C:36](Cl)=[O:37]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:21])[C:6]1[N:7]=[CH:8][C:9]([N:19]([CH3:20])[C:36](=[O:37])[C:35]2[CH:34]=[C:33]([C:32]([F:47])([F:46])[F:31])[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 70663212HCID 70663212, compound

Product 1

HCID 86670690HCID 86670690, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N2-(2-methoxyethyl)-N2,N5-dimethyl-4-o-tolylpyridine-2,5-diamine (32 mg, 0.11 mmol) and DIPEA (43 μL, 0.25 mmol) in CH2Cl2 (1 mL) was treated with 3,5-bis-trifluoromethylbenzoyl chloride (46 mg, 0.17 mmol, CAS RN 1271-19-8). After stirring for 1 h, the reaction mixture was loaded directly onto a silica gel column. Elution with 25% EtOAc in n-hexane afforded the title compound as a yellow solid (19 mg, 33%). MS (ESI): m/z=526.2 [M+H]+.

Workup

  1. washElution with 25% EtOAc in n-hexane

Sources & evidence

ORD record
ord-7756a290a5344527b47f0c6c56771b13
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…