Ethyl Acetate → HCID 86657980, compound

HRID 2366812Notes

Reaction equation

HRID 2366812 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[C:29]=2[CH:30]=1.Cl.C(N=C=N[CH2:41][CH2:42][CH2:43]N(C)C)C.C(OCC)(=[O:49])C>CN(C)C=O.O>[CH3:24][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:41](=[O:49])[C:42]#[C:43][C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:30]=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 86657980HCID 86657980, compoundYield 11%

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-phenylprop-2-ynoic acid (21 mg, 0.15 mmol), HOBt (20 mg, 0.15 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (28 mg, 0.15 mmol) 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. The residue was dissolved in dimethyl sulfoxide, and purified by preparative HPLC. The obtained fraction was concentrated to give the title compound (6.3 mg, 11%) as a powder.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dimethyl sulfoxide
  3. custompurified by preparative HPLC
  4. concentrationThe obtained fraction was concentrated

Sources & evidence

ORD record
ord-8ce9a19534af433bb594512fc6913018
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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