Diisopropylethylamine → HCID 178429146, compound

HRID 1158113Notes

Reaction equation

HRID 1158113 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][C:11]([CH2:16][CH2:17][OH:18])([CH3:15])[C:12](=[O:14])[N:13]=1.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:20]([O:18][CH2:17][CH2:16][C:11]1([CH3:15])[S:10][C:9]([NH:8][CH:2]2[CH2:3][CH:4]3[CH2:7][CH:1]2[CH2:6][CH2:5]3)=[N:13][C:12]1=[O:14])(=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 178429627HCID 178429627, compound

Product 1

HCID 178429146HCID 178429146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(bicyclo[2.2.1]heptan-2-ylamino)-5-(2-hydroxyethyl)-5-methylthiazol-4(5H)-one (0.080 g, 0.30 mmol), isonicotinoyl chloride hydrochloride (0.056, 0.30 mmol), and N,N-diisopropylethylamine (0.13 mL, 0.75 mmol) in CH2Cl2 (1.0 mL) was heated in a sealed tube in a microwave oven (SmithSynthesizer from Personal Chemistry) at 120° C. for 10 min. The reaction mixture was conc. in vacuo, and the residue was partitioned between EtOAc and water. The organic portion was separated, washed with brine, conc. in vacuo, and purified by RP-HPLC to give the title compound as a white solid. MS m/z: 374.1 (M+H)+.

Workup

  1. customthe residue was partitioned between EtOAc and water
  2. customThe organic portion was separated
  3. washwashed with brine, conc. in vacuo
  4. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-a53bb7c99f684047b07c2018c8b34983
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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