Ethyl Acetate → HCID 86657979, compound

HRID 2366811Notes

Reaction equation

HRID 2366811 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([CH:23]=1)[O:7][C:8]1[N:13]=[C:12]2[S:14][C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])=[N:16][C:11]2=[CH:10][CH:9]=1.[CH:25]1[CH:26]=[CH:27][C:28]2N(O)N=[N:31][C:29]=2[CH:30]=1.Cl.[CH2:36](N=C=NCCCN(C)C)C.[C:47](OCC)(=[O:49])C>CN(C)C=O.O>[CH3:24][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:47](=[O:49])/[CH:28]=[CH:27]/[C:26]2[CH:36]=[N:31][CH:29]=[CH:30][CH:25]=2)=[CH:23][C:6]=1[O:7][C:8]1[N:13]=[C:12]2[S:14][C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])=[N:16][C:11]2=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58451281HCID 58451281, compound

Product 1

HCID 86657979HCID 86657979, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-[5-(5-amino-2-methylphenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (41 mg, 0.12 mmol) produced in Reference Example 1,3-(3-pyridyl)acrylic acid (22 mg, 0.15 mmol), HOBt (20 mg, 0.15 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (28 mg, 0.15 mmmo) in N,N-dimethylformamide (3 mL) was stirred at room temperature overnight. Ethyl acetate (3 mL) and water (3 mL) were added to the reaction mixture, and the organic layer was dehydrated with Presep Tube manufactured by Wako Pure Chemical Industries, Ltd, and concentrated. Dimethyl sulfoxide was added to the residue, and methanol was further added. The precipitate was collected by filtration, washed with methanol and dried to give the title compound (28.6 mg, 51%) as a powder.

Workup

  1. concentrationconcentrated
  2. additionDimethyl sulfoxide was added to the residue, and methanol
  3. additionwas further added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with methanol
  6. customdried

Sources & evidence

ORD record
ord-60fa24f810d74266a14199df51e61af3
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

Loading…