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

HRID 2080215
ノート
印刷プレビュー

反応式

HRID 2080215 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.[CH:11]1([CH:14]=[CH:15][C:16]2[S:20][C:19]([CH2:21][NH2:22])=[CH:18][CH:17]=2)[CH2:13][CH2:12]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.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:22][CH2:21][C:19]2[S:20][C:16]([CH:15]=[CH:14][CH:11]3[CH2:13][CH2:12]3)=[CH:17][CH:18]=2)=[O:8])=[CH:4][N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 67119557C-(5-(2-Cyclopropylvinyl)thiophen-2-yl)methylamine

生成物 1

HCID 671196356-Amino-N-(5-(2-cyclopropylvinyl)thiophen-2-ylmethyl)nicotinamide収率 66.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

6-Aminonicotinic acid (35 mg, 0.251 mmol), C-(5-(2-cyclopropylvinyl)thiophen-2-yl)methylamine described in Preparation Example 151 (45 mg, 0.251 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (133 mg, 0.301 mmol) and triethylamine (0.042 mL, 0.301 mmol) were dissolved in N,N-dimethylformamide (3 mL), and the solution was stirred at room temperature for 3 hours. Water (10 mL) was added to the reaction solution, which was then extracted with ethyl acetate (30 mL). The organic layer was washed, dried over anhydrous magnesium sulfate, then, the solvent was evaporated in vacuo, the obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1), and the title compound (50 mg, 0.167 mmol, 66.6%) was obtained as a white solid.

後処理

  1. extractionwas then extracted with ethyl acetate (30 mL)
  2. washThe organic layer was washed
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customthe obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-7e48cadb1bcd4b22951a1201446d9ef8
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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