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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-Butyl 4-({[(2-chloro-5-fluoropyridin-3-yl)carbonyl]amino}methyl)benzoate

HRID 1293175
ノート
印刷プレビュー

反応式

HRID 1293175 の反応式
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:12][CH2:13][C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>ClCCl.O.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([C:4]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[CH:25][CH:26]=2)=[O:6])=[CH:7][C:8]([F:11])=[CH:9][N:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 114352432-Chloro-5-fluoronicotinic acidHCID 14514888tert-Butyl 4-(aminomethyl)benzoate

生成物 1

HCID 86627076tert-Butyl 4-({[(2-chloro-5-fluoropyridin-3-yl)carbonyl]amino}methyl)benzoate収率 82%

試薬・触媒・溶媒

3
HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

To a stirred solution of 2-chloro-5-fluoronicotinic acid (2.0 g, 10 mmol) and tert-butyl 4-(aminomethyl)benzoate (1.65 g, 8 mmol) in dichloromethane (25 mL) were successively added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (2.88 g, 15 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (1.53 g, 10 mmol), and triethylamine (5 mL). After being stirred overnight, the reaction mixture was poured into water (100 mL). The organic layer_was separated and the aqueous layer was extracted with dichloromethane (50 mL×2). The combined organic layers were washed with brine (100 mL), dried (sodium sulfate), and evaporated. The residue was purified by flush column chromatography on silica gel (200 g) eluting with dichloromethane/ethyl acetate (20/1) to afford 2.39 g (82%) of the title compounds as white solids: 1H-NMR (CDCl3) δ 8.33 (1H, d, J=3.1 Hz), 7.97 (2H, d, J=8.4 Hz), 7.91 (1H, dd, J=7.9, 3.1 Hz), 7.40 (2H, d, J=8.4 Hz), 7.04 (1H, br.s), 4.70 (2H, d, J=5.9 Hz), 1.58 (9H, s).

後処理

  1. customThe organic layer_was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (50 mL×2)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe residue was purified
  7. customby flush column chromatography on silica gel (200 g)
  8. washeluting with dichloromethane/ethyl acetate (20/1)

出典と根拠

ORDレコード
ord-89aaa8a8182a4f408492dd3223c26f51
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07238714B2

反応ノート

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