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Triethylamine → (3-{[(6-Oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-propyl)-carbamic acid tert-butyl ester

HRID 333223
ノート
印刷プレビュー

反応式

HRID 333223 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].[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30][NH2:31])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C>CN(C)C=O>[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30][NH:31][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)([CH3:24])([CH3:22])[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide

生成物 1

HCID 66819479(3-{[(6-Oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-propyl)-carbamic acid tert-butyl ester収率 44.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
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) (50 mg, 0.17 mmol) in N,N-dimethylformamide (2 mL), (3-amino-propyl)-carbamic acid tert-butyl ester (0.09 mL, 0.51 mmol) and triethylamine (0.036 mL, 0.26 mmol) were added. The reaction mixture was stirred at room temperature overnight, evaporated to dryness and then purified through by preparative HPLC on a 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 32 mg (44% yield) of the title compound.

後処理

  1. additionwere added
  2. customevaporated to dryness
  3. custompurified through by preparative HPLC on a Waters X Terra RP 18 (19×250 mm, 5 μm) column
  4. waitGradient from 10 to 75% B in 15 min
  5. additionFractions containing the desired compound
  6. customwere dried

出典と根拠

ORDレコード
ord-0542c9c8f9eb418981ce8057a7a131cf
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877944B2

反応ノート

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