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Triethylamine → Imidazo[1,2-a]pyridine-6-carboxamide,n-[[5-(3-fluorophenoxy)-2-thienyl]methyl]-

HRID 2080006
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HRID 2080006 반응식
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=12.[F:13][C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=1)[O:17][C:18]1[S:22][C:21]([CH2:23][NH2:24])=[CH:20][CH:19]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[F:13][C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=1)[O:17][C:18]1[S:22][C:21]([CH2:23][NH:24][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=2)=[O:12])=[CH:20][CH:19]=1
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 7075376Imidazo(1,2-a)pyridine-6-carboxylic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130606C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine

생성물 1

HCID 58387866Imidazo[1,2-a]pyridine-6-carboxamide,n-[[5-(3-fluorophenoxy)-2-thienyl]methyl]-수율 46.3%

시약·촉매·용매

3
HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매3회

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온도
80 °C

실험 절차

To a solution of imidazo[1,2-a]pyridine-6-carboxylic acid (87 mg, 0.54 mmol) and C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine (120 mg, 0.54 mmol) in N,N-dimethylformamide (5 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (240 mg, 0.54 mmol) and triethylamine(0.15 mL, 1.08 mmol), and the solution was stirred for 40 minutes at 80° C. Water and ethyl acetate were added to the reaction mixture for extraction, and the organic layer was washed twice with water. Silica gel was added to the organic layer, solvent was evaporated in vacuo for adsorption, purification was carried out by silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate), and the title compound (90 mg, 0.25 mmol, 45.4%) was obtained as a light brown oil.

후처리

  1. washthe organic layer was washed twice with water
  2. additionSilica gel was added to the organic layer, solvent
  3. customwas evaporated in vacuo for adsorption, purification

출처 및 근거

ORD 기록
ord-336412bd8be14347a47b206ea71aa70e
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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