1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-Benzyl-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl azetidine-3-carboxamide

HRID 1024497ノート

反応式

HRID 1024497 の反応式
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1.[CH2:19]([N:26]1[CH2:29][CH:28]([C:30]([OH:32])=O)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C(N=C=NCCCN(C)C)C.CC1C=CN=C(N)C=1C>ClCCl.O>[CH2:19]([N:26]1[CH2:27][CH:28]([C:30]([N:14]([CH2:13][C:4]2[CH:3]=[C:2]([Cl:1])[C:7]3[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=3[CH:5]=2)[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:32])[CH2:29]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

7

反応物 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 31613181-Benzylazetidine-3-carboxylic acidHCID 110078842-Amino-3,4-dimethylpyridineHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

生成物 1

HCID 580804741-Benzyl-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl azetidine-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

40 mg of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine was combined with 28 mg of 1-benzyl-azetidine-3-carboxylic acid in 5 ml dichloromethane. 38 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 26 mg of dimethyl aminopyridine were added. The reaction solution was stirred at room temperature overnight. 5 ml of water was added and the mixture was extracted with 5 ml ethyl acetate three times. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium phosphate and concentrated under reduced pressure. The product was purified by column chromatography using 75% ethyl acetate in hexane as a resin: MS (m+1)=443.3; 1H NMR (500 MHz, CDCl3) 0.95 (m, 6H), 1.95 (m, 1H), 2.05 (m, 1H), 2.25 (m, 2H), 2.95 (d, 1H), 3.00 (d, 1H), 3.40 (m, 1H), 3.45 (m, 1H), 3.50 (m, 1H), 3.65 (m, 2H), 3.75 (m, 2H), 4.25 (m, 2H), 4.35 (m, 2H), 4.50 (s, 1H), 6.5-7.0 (m, 2H), 7.1-7.4 (m, 5H).

後処理

  1. extractionthe mixture was extracted with 5 ml ethyl acetate three times
  2. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous sodium phosphate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by column chromatography

出典と根拠

ORDレコード
ord-4f0314a295be43d48a7bce2504ac5e31
出典データセット
uspto-grants-2014_05
特許番号
US08722896B2

反応ノート

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