1-Hydroxybenzotriazole → HCID 59170262、化合物

HRID 1446151ノート

反応式

HRID 1446151 の反応式
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:2]1.[C:12]1([C:18]2[O:22][N:21]=[CH:20][C:19]=2[C:23](O)=[O:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN1CCCC1=O>[C:12]1([C:18]2[O:22][N:21]=[CH:20][C:19]=2[C:23]([N:1]2[CH2:5][CH2:4][CH:3]([C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[CH2:2]2)=[O:24])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 147872535-Phenylisoxazole-4-carboxylic acid

生成物 1

HCID 59170262HCID 59170262、化合物収率 50.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

To a 15 mL round-bottomed flask equipped with magnetic stirring was added 3-(pyrrolidin-3-yl)pyridine (250 mg, 1700 μmol, source: ASDI Inc.) and 4 mL of N-methylpyrrolidinone (NMP). 5-Phenylisoxazole-4-carboxylic acid (300 mg, 1600 μmol, source: CiVentiChem) was added followed by 1-hydroxybenzotriazole (250 mg, 1800 μmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (380 mg, 2000 μmol). Added 2 mL more NMP, and the reaction mixture was stirred at ambient temp. After 3 days, added 30 mL of water and extracted with EtOAc (3×15 mL). The organic layers were combined, washed with sat'd NaHCO3 and brine. The organic layers were then dried over MgSO4, filtered and concentrated in vacuo. The sample was absorbed onto silica gel and purified on a 40 g Isco Redi-sep® silica gel column that had been pre-equilibrated with CH2Cl2+2% MeOH. The product was eluted sample with CH2Cl2+2% (2M NH3 in MeOH). A viscous yellow oil was isolated as desired product (mass=260 mg). Mass Spec. m/z+ion=320.1.

後処理

  1. customTo a 15 mL round-bottomed flask equipped
  2. stirringthe reaction mixture was stirred at ambient temp
  3. extractionextracted with EtOAc (3×15 mL)
  4. washwashed with sat'd NaHCO3 and brine
  5. dry with materialThe organic layers were then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe sample was absorbed onto silica gel
  9. custompurified on a 40 g Isco Redi-sep® silica gel column that
  10. washThe product was eluted sample with CH2Cl2+2% (2M NH3 in MeOH)

出典と根拠

ORDレコード
ord-340226b01309425e8a5f1586155368ba
出典データセット
uspto-grants-2010_02
特許番号
US07666888B2

反応ノート

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