Triethylamine → HCID 66930848、化合物

HRID 1364137ノート

反応式

HRID 1364137 の反応式
Cl.Cl.[NH:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)[NH2:4].O=[C:19]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21][CH:20]1[C:33](OCC)=[O:34].C(N(CC)CC)C>C(O)(C)(C)C>[O:34]=[C:33]1[CH:20]2[C:19]([CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[N:4][N:3]1[CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylateHCID 211931571-Benzyl-4-hydrazinylpiperidine dihydrochloride

生成物 1

HCID 66930848HCID 66930848、化合物

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A mixture of 4-hydrazino-1-(phenylmethyl)piperidine dihydrochloride (commercially available from e.g. Aurora Screening Library) (2.68 g, 9.63 mmol) and tert-butanol (60 ml) was added to 1-(1,1-dimethylethyl) 4-ethyl 5-oxohexahydro-1H-azepine-1,4-dicarboxylate (may be prepared as described in Synthetic Communications (1992), 22(9), 1249-58) (2.50 g, 8.76 mmol) followed by triethylamine (7.33 ml, 52.59 mmol) and the resulting suspension warmed to reflux over ˜10 min under Argon. The resulting clear yellow solution was then kept at this temperature for 65 h. The mixture was then allowed to cool to room temperature over ˜2 h and the mixture reduced under vacuum to give a cream coloured solid residue. Purification by chromatography on silica gel eluting with dichloromethane:methanol 50:1→25:1→10:1 afforded a product which as partitioned between water and dichloromethane (100 ml each) the layers separated and the organic layer washed with more water (100 ml), followed by brine (100 ml) and then dried (Na2SO4), filtered and reduced to give the title compound (D47). MS (ES+) m/e 427 [M+H]+.

後処理

  1. temperaturethe resulting suspension warmed
  2. temperatureto reflux over ˜10 min under Argon
  3. customto give a cream
  4. customPurification by chromatography on silica gel eluting with dichloromethane:methanol 50:1→25:1→10:1
  5. customafforded a product which
  6. customas partitioned between water and dichloromethane (100 ml each) the layers
  7. customseparated
  8. washthe organic layer washed with more water (100 ml)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-5b10e7072b984ff582194fb512926721
出典データセット
uspto-grants-2011_02
特許番号
US07888347B2

反応ノート

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