Diisopropylethylamine → HCID 178429146, compound

HRID 852802Notes

Reaction equation

HRID 852802 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-ca91ea028be74bf99f28e67fc6f8b172
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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