1-Hydroxybenzotriazole → HCID 178509858、化合物

HRID 1093816ノート

反応式

HRID 1093816 の反応式
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[NH:51]1[CH2:56][CH2:55][CH:54]([O:57][C:58]2[CH:59]=[C:60]([CH:63]=[CH:64][CH:65]=2)[C:61]#[N:62])[CH2:53][CH2:52]1>CN(C=O)C.O>[C:61]([C:60]1[CH:59]=[C:58]([CH:65]=[CH:64][CH:63]=1)[O:57][CH:54]1[CH2:55][CH2:56][N:51]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:18]2[CH:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:20][N:19]=2)=[O:22])[CH2:52][CH2:53]1)#[N:62]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 534337453-(Piperidin-4-yloxy)benzonitrile hydrochlorideHCID 178525878HCID 178525878、化合物

生成物 1

HCID 178509858HCID 178509858、化合物収率 14.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (316 mg, 2.5 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (181 mg, 0.7 mmol) in DMF (3 mL) followed by HOBt (108 mg, 0.8 mmol) and EDCI.HCl (160 mg, 0.8 mmol). After 2 minutes of stirring, 3-(piperidin-4-yloxy)-benzonitrile hydrochloride (50 mg, 0.7 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine and concentrated The residue was purified by column chromatography (using neutral alumina and 5% MeOH in CHCl3) afford 44 mg (14.3% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(3-cyano-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 473.17, 99.16%, 1H NMR (300 MHz, DMSO-d6): δ 8.1 (m, 1H), 7.8 (m, 2H), 7.6 (m, 4H), 7.4 (m, 3H), 7.1 (b, 1H), 4.8 (m, 1H), 4.2 (m, 2H), 4.0 (m, 1H), 3.8 (m, 1H), 2.0 (m, 2H), 1.5 (m, 2H).

後処理

  1. additionwas added
  2. stirringstirring
  3. waitwas continued at ambient temperature overnight
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. concentrationconcentrated The residue
  7. customwas purified by column chromatography (using neutral alumina and 5% MeOH in CHCl3)

出典と根拠

ORDレコード
ord-60f21ee701be492c8ff539a6b8b80404
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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