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Triethylamine → 2-Chloro-N-[(5-phenoxythiophen-2-yl)methyl]pyridine-3-carboxamide

HRID 2079965
ノート
印刷プレビュー

反応式

HRID 2079965 の反応式
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[O:11]([C:18]1[S:22][C:21]([CH2:23][NH2:24])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:24][CH2:23][C:21]1[S:22][C:18]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:19][CH:20]=1)=[O:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 762582-Chloronicotinic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23130515C-(5-Phenoxy thiophen-2-yl)methylamine

生成物 1

HCID 231303812-Chloro-N-[(5-phenoxythiophen-2-yl)methyl]pyridine-3-carboxamide収率 46%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-chloro nicotinic acid (1182 mg, 7.50 mmol) in N,N-dimethylformamide (3 mL) were added C-(5-phenoxy-thiophen-2-yl)methylamine described in Preparation Example 24 (1693 mg, 8.25 mmol), benzotriazol-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (3987 mg, 9.0 mmol) and triethylamine (2.5 mL, 18.0 mmol), and the solution was stirred at 60° C. for 2 days. Water was added to the reaction mixture, which was then extracted with ethyl acetate, and then concentrated. The residue was purified by silica gel column chromatography, and the title compound (1181 mg, 3.43 mmol, 46%) was obtained.

後処理

  1. extractionwas then extracted with ethyl acetate
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-eb63640d58bc414b8ceb3ec9b91d010b
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932272B2

反応ノート

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