1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57572271、化合物

HRID 1293161ノート

反応式

HRID 1293161 の反応式
[F:1][C:2]1[CH:3]=[N:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:20][CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>ClCCl.C(N(CC)CC)C>[F:1][C:2]1[CH:10]=[C:6]([C:7]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=2)=[O:9])[C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][CH:3]=1

参加物

7

反応物 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 575722785-Fluoro-2-(4-fluorophenoxy)nicotinic acid

生成物 1

HCID 57572271HCID 57572271、化合物収率 85.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

To a stirred solution of 5-fluoro-2-(4-fluorophenoxy)nicotinic acid (step 2, 300 mg, 1.2 mmol) and methyl 4-(aminomethyl)benzoate hydrochloride (284 mg, 1.4 mmol) in dichloromethane (10 mL) were successively added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (670 mg, 3.5 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (368 mg, 2.4 mmol), and triethylamine (3 mL). After being stirred overnight, the reaction was quenched by the addition of saturated sodium bicarbonate aqueous solution (50 mL). The aqueous layer was extracted with dichloromethane (50 mL×2) and the combined organic layers were washed with brine (50 mL), dried (sodium sulfate), and evaporated. The remaining residue was purified by flush column chromatography on silica gel (50 g) eluting with hexane/ethyl acetate (3/1) to afford 407 mg (85%) of the title compounds as white solids: 1H-NMR (CDCl3) δ 8.39 (1H, dd, J=8.3, 3.1 Hz), 8.28 (1H, br.s), 8.05 (1H, d, J=3.1 Hz), 8.01 (2H, d, J=8.1 Hz), 7.42 (2H, d, J=8.1 Hz), 7.17–7.05 (4H, m), 4.76 (2H, d, J=5.9 Hz), 3.91 (3H, s); MS (ESI) m/z 399 (M+H)+, 397 (M−H)−.

後処理

  1. customthe reaction was quenched by the addition of saturated sodium bicarbonate aqueous solution (50 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (50 mL×2)
  3. washthe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe remaining residue was purified
  7. customby flush column chromatography on silica gel (50 g)
  8. washeluting with hexane/ethyl acetate (3/1)

出典と根拠

ORDレコード
ord-4346d93d5fd540b78c39faeedcd85776
出典データセット
uspto-grants-2007_07
特許番号
US07238714B2

反応ノート

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