Ammonium Chloride → 5-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

HRID 2060637Notes

Reaction equation

HRID 2060637 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:19]([OH:21])=O.O[N:23]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>CN(C)C=O>[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:19]([NH2:23])=[O:21]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 583352705-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid

Product 1

HCID 583352605-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid (310 mg, 1.01 mmol), 1-hydroxybenzotriazole (310 mg, 2.02 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (388 mg, 2.02 mmol), and ammonium chloride (271 mg, 5.06 mmol) were taken up in dimethylformamide (20 mL) under argon. Diisopropylethylamine (0.88 mL, 5.06 mmol) was added and the mixture was stirred at ambient temperature for 36 hours. The mixture was then concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-10% methanol/ethyl acetate) to afford the title compound. LRMS (APCI) calc'd for (C13H16N5O2S) [M+H]+, 306.1; found 306.0.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe resulting residue was purified via flash chromatography (silica, 0-10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-8e9955962ca244eb87852a38071c15ec
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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