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

HRID 2079959
ノート
印刷プレビュー

反応式

HRID 2079959 の反応式
[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
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

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c34d88ad764542a390acfddc6744389b
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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