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2,4,6-Tris((dimethylamino)methyl)phenol → N-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxamide

HRID 1894716
ノート
印刷プレビュー

反応式

HRID 1894716 の反応式
CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.[F:20][C:21]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[C:22]=1[C:23]([C:25]1[CH:26]=[C:27]([C:30]([OH:32])=O)[NH:28][CH:29]=1)=[O:24].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:63][C:64]1[S:68][C:67]([CH2:69][NH2:70])=[N:66][N:65]=1.C(N(C(C)C)CC)(C)C>>[CH3:63][C:64]1[S:68][C:67]([CH2:69][NH:70][C:30]([C:27]2[NH:28][CH:29]=[C:25]([C:23](=[O:24])[C:22]3[C:33]([F:38])=[CH:34][C:35]([F:37])=[CH:36][C:21]=3[F:20])[CH:26]=2)=[O:32])=[N:66][N:65]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 6

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11615231(5-Methyl-1,3,4-thiadiazol-2-yl)methanamine hydrochlorideHCID 534025784-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid
2 回

生成物 1

HCID 49784129N-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxamide収率 69.3%

実験手順

To a DMF 3 mL solution of 4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxylic acid (Intermediate 1) (30 mg, 0.11 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (22 mg, 0.15 mmol) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide-hydrochloride (EDC-hydrochloride)(28 mg, 0.15 mmol). The reaction was stirred for 45 min before 1-(5-methyl-1,3,4-thiadiazol-2-yl)methanamine hydrochloride (19 mg, 0.17 mmol) and diisopropylethylamine (0.1 mL, 0.55 mmol) were added. The reaction mixture was stirred at rt overnight, concentrated and chromatographed on silica gel eluting with AcOEt to give the title compound 29 mg.

後処理

  1. additionwere added
  2. concentrationconcentrated
  3. customchromatographed on silica gel eluting with AcOEt

出典と根拠

ORDレコード
ord-2253231ca8d441b7b415a3fdee4b5f1b
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08513289B2

反応ノート

読み込み中…

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