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1,2-Dichloroethane → N-4-Isoxazolyl-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

HRID 1623804
ノート
印刷プレビュー

反応式

HRID 1623804 の反応式
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][C:10]=2[C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=C[C:31]2[N:36]([OH:37])N=[N:34][C:32]=2[CH:33]=1.O1C=C(N)C=N1>CN(C)C=O.O>[O:37]1[CH:33]=[C:32]([NH:34][C:11](=[O:12])[C:10]2[CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][C:9]=2[O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:31]=[N:36]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 138042781,2-Oxazol-4-amineHCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

生成物 1

HCID 68108909N-4-Isoxazolyl-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 100 mg, 0.30 mmol), EDC (172 mg, 0.90 mmol) and HOBT (137 mg, 0.90 mmol) in dimethylformamide (3 ml) was stirred in air at room temperature for 1 h, then 4-isoxazolamine (may be prepared as described in Description 95; 100 mg, 1.189 mmol) was added in one charge. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (30 ml). The solid was filtered and dried in vacuo to obtain crude product, which was purified with Prep-HPLC (Waters, X-Bridge, 5 μm; 30×100 mm; A=0.05% NH3.H2O/water, B: MeCN; v=30 ml/min; 0-7 min, 42%-54%; 7-12 min, 95%; t=8.0 min.) to yield the title compound as a white solid. 34 mg.

後処理

  1. additioncharge
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. filtrationThe solid was filtered
  4. customdried in vacuo
  5. customto obtain crude product, which
  6. customwas purified with Prep-HPLC (Waters, X-Bridge, 5 μm
  7. custom0-7 min, 42%-54%
  8. custom7-12 min, 95%

出典と根拠

ORDレコード
ord-d02bee0e53674fd5b0a272d6a2897f82
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08778939B2

反応ノート

読み込み中…

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