Benzylamine → 2-Amino-4-benzylthiazole-5-carboxylic Acid Benzylamide

HRID 45315ノート

反応式

HRID 45315 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:14]([OH:16])=O)=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:48]([NH2:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:48]([NH:55][C:14]([C:4]1[S:3][C:2]([NH2:1])=[N:6][C:5]=1[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:16])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

参加物

8

反応物 5

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 822255112-Amino-4-benzylthiazole-5-carboxylic acid

生成物 1

HCID 866425132-Amino-4-benzylthiazole-5-carboxylic Acid Benzylamide収率 65%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-amino-4-benzylthiazole-5-carboxylic acid (0.033 g, 0.14 mmol) and diisopropylethylamine (0.08 mL, 0.46 mmol) in N,N-dimethylformamide (5 mL) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.039 g, 0.20 mmol), followed by the addition of 1-hydroxybenzotriazole (0.026 g, 0.19 mmol). After 30 minutes, benzylamine (0.02 mL, 0.18 mmol) was added. The reaction mixture was stirred at ambient temperature for 12 h, diluted with ethyl acetate, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford the title compound (0.029 g, 65% yield).

後処理

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography
  6. washeluting with ethyl acetate/hexanes (5/95 to 100/0)

出典と根拠

ORDレコード
ord-3f803fe591544eb0ae89adf6407e75c4
出典データセット
uspto-grants-2013_09
特許番号
US08541457B2

反応ノート

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