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1-Hydroxybenzotriazole → 5-Chloroisoquinolin-4-carboxylic amide

HRID 1470506
ノート
印刷プレビュー

反応式

HRID 1470506 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([OH:14])=O)=[CH:5][N:6]=[CH:7]2.CC[N:17](C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C1COCC1.CCOC(C)=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([NH2:17])=[O:14])=[CH:5][N:6]=[CH:7]2
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 682819645-Chloroisoquinoline-4-carboxylic acid

生成物 1

HCID 682818935-Chloroisoquinolin-4-carboxylic amide収率 70%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A 100 mL RBF was charged with 5-chloroisoquinolin-4-carboxylic acid (1 equiv) in dry THF (20 mL), DIPEA (3 equiv), EDC.HCl (1.5 equiv), HOBT (1.5 equiv) under inert atmosphere and the mixture was stirred for 15 mins. To this, corresponding amine (1.2 equiv) was added dropwise and the reaction mixture was stirred overnight. After completion, it was diluted with EtOAc and water. The organic layer was then separated, dried and concentrated under reduced pressure to give the crude product that was purified by column chromatography using 100-200 silica gel (80% Ethyl acetate in Hexanes) to furnish the desired amide derivative in 70-84% yield.

後処理

  1. stirringthe reaction mixture was stirred overnight
  2. customThe organic layer was then separated
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product that
  6. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-0f4b566d253a4322a9b310816c4f3244
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006442B2

反応ノート

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