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

HRID 1623804
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HRID 1623804 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water
용매
HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-d02bee0e53674fd5b0a272d6a2897f82
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778939B2

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