Triethylamine → HCID 484993、化合物

HRID 1383401ノート

反応式

HRID 1383401 の反応式
Cl.[Br:2][C:3]1C=C[C:6]([CH2:7]N)=[CH:5][CH:4]=1.C([N:13]([CH2:16][CH3:17])CC)C.[N:18]1[C:27]2[C:22](=[CH:23][N:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28]([OH:30])=O.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O>[Br:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:17]=1[CH2:16][NH:13][C:28]([C:19]1[CH:20]=[CH:21][C:22]2[C:27](=[CH:26][CH:25]=[N:24][CH:23]=2)[N:18]=1)=[O:30]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27240964-Bromobenzylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 484993HCID 484993、化合物収率 99%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a stirring solution of 4-bromobenzylamine hydrochloride (97.8 mg, 98%, 0.431 mmol) in anhydrous DMF (5 ml) was added triethylamine (60.1 ul. 0.431 mmol), After 5 min, 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol), 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (60.6 mg, 0.316 mmol) was sequentially added. The resulting mixture was allowed to stir at room temperature for overnight and it was found to be clear. The solvent was removed under vacuum and the resulting residue was redissolved in CH2Cl2 (100 ml). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum and the resulting residue was redissolved in CH2Cl2 (100 ml). The organic layer was washed with aqueous NaHCO3, dried over anhydrous MgSO4, and concentrated to give the crude mixture. Chromatography of the crude (Hex:EtOAc=1:1 to pure EtOAc) afforded desired product as white solid (97 mg, 99%): m.p. 149-150° C.

後処理

  1. customThe solvent was removed under vacuum
  2. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  3. stirringto stir at room temperature overnight
  4. customThe solvent was removed under vacuum
  5. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  6. washThe organic layer was washed with aqueous NaHCO3
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customto give the crude mixture

出典と根拠

ORDレコード
ord-5c1dffc6a33d4143b585ba635435e46c
出典データセット
uspto-grants-2001_07
特許番号
US06255318B1

反応ノート

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