1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874453、化合物

HRID 1093796ノート

反応式

HRID 1093796 の反応式
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[O:15][C:14]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)=[N:13][N:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][CH:54]([O:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[Cl:64])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[Cl:64][C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=1[O:57][CH:54]1[CH2:53][CH2:52][N:51]([C:49](=[O:50])[CH2:48][NH:47][C:20](=[O:22])[C:19]2[CH:18]=[CH:17][C:16]([C:14]3[O:15][C:11]([CH3:10])=[N:12][N:13]=3)=[CH:24][CH:23]=2)[CH2:56][CH2:55]1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 177237644-(5-Methyl-1,3,4-oxadiazol-2-yl)benzoic acidHCID 665915282-Amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride

生成物 1

HCID 57874453HCID 57874453、化合物収率 22.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (180 mg, 1.47 mmol) was added to a stirred solution of 1 4-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzoic acid (100 mg, 0.48 mmol) in DMF (2 mL) followed by HOBt (79 mg, 0.58 mmol) and EDCI (113 mg, 0.587 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (179 mg, 0.587 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure The residue was purified by preparative HPLC to afford 50 mg (22.52% Yield) of N-{2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-4-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzamide. LC/MS [M+H]+: 93.97%. 1H NMR (300 MHz, DMSO-d6): δ 8.8 (s, 1H), 8.2-7.9 (m, 4H), 7.5-7.2 (m, 3H), 7.0 (bt, 1H), 4.8 (bs, 1H), 4.2 (bs, 2H), 3.7 (bs, 2H), 3.5 (m, 2H), 2.7-2.5 (m, 3H), 2.1-1.5 (m, 4H).

後処理

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. extractionthe product was extracted with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure The residue
  7. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-d7dbffb7eb0b467cb2bff4f790f1b065
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

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