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Triethylamine → 6-Amino-N-(5-phenoxy thiophen-2-ylmethyl)-nicotinamide

HRID 2080213
ノート
印刷プレビュー

反応式

HRID 2080213 の反応式
[O:1]([C:8]1[S:12][C:11]([CH2:13][NH2:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=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.CO.C(OCC)(=O)C.O>[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:14][CH2:13][C:11]2[S:12][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)=[O:21])=[CH:18][N:17]=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 23130515C-(5-Phenoxy thiophen-2-yl)methylamine

生成物 1

HCID 231305396-Amino-N-(5-phenoxy thiophen-2-ylmethyl)-nicotinamide収率 48.2%

試薬・触媒・溶媒 4

HCID 887
Methanol
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 C-(5-phenoxythiophen-2-yl)methylamine described in Preparation Example 24 (170 mg, 0.83 mmol) and 6-aminonicotinic acid (130 mg, 0.91 mmol) in N,N-dimethylformamide (10 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (400 mg, 0.91 mmol) and triethylamine (0.3 mL, 2.2 mmol), and the solution was stirred for 35 minutes at 60° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with water twice, NH silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=50:1), and the title compound (130 mg, 0.40 mmol, 48.2%) was obtained as a solid.

後処理

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. additionNH silica 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-7593b1868c8d43b9a0e09fabd4404900
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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