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

HRID 2079965
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HRID 2079965 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-eb63640d58bc414b8ceb3ec9b91d010b
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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