Triethylamine → (6-{[(6-Oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-hexyl)-carbamic acid tert-butyl ester

HRID 333224ノート

反応式

HRID 333224 の反応式
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)=[O:4].Cl.[C:22]([O:26][C:27](=[O:36])[NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>CN(C)C=O.ClCCl>[C:22]([O:26][C:27](=[O:36])[NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:2][C:3](=[O:4])[NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)([CH3:25])([CH3:23])[CH3:24]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 3017638N-Boc-1,6-diamino-hexane hydrochlorideHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide

生成物 1

HCID 66819636(6-{[(6-Oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-hexyl)-carbamic acid tert-butyl ester収率 47%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of 2-chloro-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide (XVIII, Lg=Cl, 65 mg, 0.23 mmol) in N,N-dimethylformamide (2 mL), (6-amino-hexyl)-carbamic acid tert-butyl ester hydrochloride (175 mg, 0.69 mmol) and triethylamine (0.097 mL, 0.69 mmol) were added. The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane, and the resulting solution was washed with water then brine, dried over sodium sulfate and evaporated to dryness. The crude was purified by preparative HPLC on Waters X Terra RP 18 (19×250 mm, 5 μm) column. Mobile phase A was 0.05% ammonium hydroxide/acetonitrile:95/5 and mobile phase B was acetonitrile/water:95/5. Gradient from 10 to 75% B in 15 min. Fractions containing the desired compound were dried, affording 50 mg (47% yield) of the title compound.

後処理

  1. additionwere added
  2. washthe resulting solution was washed with water
  3. dry with materialbrine, dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude was purified by preparative HPLC on Waters X Terra RP 18 (19×250 mm, 5 μm) column
  6. waitGradient from 10 to 75% B in 15 min
  7. additionFractions containing the desired compound
  8. customwere dried

出典と根拠

ORDレコード
ord-fe9b7f9616ad42e488c73c8a5424055c
出典データセット
uspto-grants-2014_11
特許番号
US08877944B2

反応ノート

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