Triethylamine → (+/-)-2-methyl-cyclohexanecarboxylic acid-N'-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazide

HRID 1808706

反応式

HRID 1808706 の反応式
Cl.[CH3:2][Si:3]([CH3:20])([CH3:19])[CH2:4][CH2:5][O:6][CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[C:15]([NH:17][NH2:18])[N:16]=[C:11]2[CH:10]=[CH:9]1.[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:28](O)=[O:29].C(N(CC)CC)C.CCN=C=NCCCN(C)C>ClCCl>[CH3:2][Si:3]([CH3:20])([CH3:19])[CH2:4][CH2:5][O:6][CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[C:15]([NH:17][NH:18][C:28]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]3[CH3:21])=[O:29])[N:16]=[C:11]2[CH:10]=[CH:9]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 858112-Methylcyclohexanecarboxylic acidHCID 66839317[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazine hydrochloride

生成物 1

HCID 86650161(+/-)-2-methyl-cyclohexanecarboxylic acid-N'-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazide収率 35.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A flask containing a mixture of [5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazine hydrochloride (336 mg, 1.06 mmol) and (+/−)-2-methyl-1-cyclohexane-carboxylic acid (0.18 mL, 1.22 mmol) in dry dichloromethane (11 mL) was cooled to 0° C. (ice bath) under nitrogen atmosphere. To this cooled mixture was added triethylamine (0.31 mL, 2.1 mmol) and EDCI (278 mg, 1.45 mmol). After 30 minutes the cooling bath was removed and the material was stirred for 3 hours. An aqueous solution of 5% sodium bicarbonate (40 mL) and methylene chloride (30 mL) were added and the mixture was shaken in a reparatory funnel. The organic phase was collected and washed with brine (40 mL). The aqueous phases were back extracted with methylene chloride (2×30 mL). The organic phases were combined, dried (MgSO4), filtered and stripped. The crude remainder was purified by preparative TLC, using 45% ethyl acetate in hexanes to elute. The product band was collected, affording 152 mg of (+/−)-2-methyl-cyclohexanecarboxylic acid-N′-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazide as a golden brown oil, which solidified on standing. MS (M+H)+=404.

後処理

  1. additionA flask containing
  2. customAfter 30 minutes the cooling bath was removed
  3. additionAn aqueous solution of 5% sodium bicarbonate (40 mL) and methylene chloride (30 mL) were added
  4. stirringthe mixture was shaken in a reparatory funnel
  5. customThe organic phase was collected
  6. washwashed with brine (40 mL)
  7. extractionThe aqueous phases were back extracted with methylene chloride (2×30 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe crude remainder was purified by preparative TLC
  11. washto elute
  12. customThe product band was collected

出典と根拠

ORDレコード
ord-d2b199f5b55c45b28c7762afc2f65b66
出典データセット
uspto-grants-2013_01
特許番号
US08361962B2

関連ノート

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