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Triethylamine → 6-amino-N-(5-(3-fluoro-phenoxy)-thiophen-2-yl)-methylnicotinamide

HRID 2079959
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HRID 2079959 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][CH:25]=1)[O:15][C:16]1[S:20]C(CN)=C[CH:17]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:36]=2N=N1.C([N:54]([CH2:57][CH3:58])CC)C>CN(C)C=O.CO.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:54][C:57]2[S:20][C:16]([O:15][C:14]3[CH:23]=[CH:24][CH:25]=[C:12]([F:11])[CH:13]=3)=[CH:17][CH:58]=2)=[O:8])=[C:4]([CH3:36])[N:3]=1
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9

반응물 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130606C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine

생성물 1

HCID 231305756-amino-N-(5-(3-fluoro-phenoxy)-thiophen-2-yl)-methylnicotinamide수율 43.9%

시약·촉매·용매 4

HCID 887Methanol용매
HCID 962Water용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매2회

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온도
60 °C

실험 절차

To a solution of 6-amino-nicotinic acid (270 mg, 2.0 mmol) and C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine (400 mg, 1.8 mmol) in N,N-dimethylformamide (10 mL) were added benzotriazole-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (870 mg, 2.0 mmol) and triethylamine (0.50 mL, 3.6 mmol), and the solution was stirred for 30 minutes at 60° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed twice with water. Silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out with NH silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=10:1), and 6-amino-N-(5-(3-fluoro-phenoxy)-thiophen-2-yl)-methylnicotinamide (270 mg, 0.79 mmol, 43.9%) was obtained.

후처리

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

출처 및 근거

ORD 기록
ord-c34d88ad764542a390acfddc6744389b
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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