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

HRID 2060637노트

반응식

HRID 2060637 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8e9955962ca244eb87852a38071c15ec
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278335B2

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