Bis(2-oxo-3-oxazolidinyl)phosphinic chloride → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H-pyrazole-3-carboxylic acid [4-(3-oxo-morpholin-4-yl)-phenyl]-amide

HRID 33255

반응식

HRID 33255 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[C:17]([C:18]4[O:19][CH:20]=[CH:21][CH:22]=4)=[CH:16][C:15]([C:23](O)=[O:24])=[N:14]3)[CH:8]=2)=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][C:34]2=[O:39])=[CH:29][CH:28]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl.CCN(CC)CC>[O:39]=[C:34]1[CH2:35][O:36][CH2:37][CH2:38][N:33]1[C:30]1[CH:29]=[CH:28][C:27]([NH:26][C:23]([C:15]2[CH:16]=[C:17]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[N:14]=2)=[O:24])=[CH:32][CH:31]=1

참가 물질

6

반응물 3

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 230334811-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H-pyrazole-3-carboxylic acid

생성물 1

HCID 602079501-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H-pyrazole-3-carboxylic acid [4-(3-oxo-morpholin-4-yl)-phenyl]-amide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

To 100 mg 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H -pyrazole-3-carboxylic acid in 2 ml DCM and 0.1 ml NEt3, 62 mg 4-(4-Amino-phenyl)-morpholin-3-one and 67 mg BOP-Cl were added at RT and the mixture was stirred for 16 h. The mixture was was concentrated under reduced pressure and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid.

후처리

  1. concentrationThe mixture was was concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (
  3. washC18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA)
  4. additionThe fractions containing the product
  5. customwere evaporated
  6. customto yield a white solid

출처 및 근거

ORD 기록
ord-af17968064c44cdd8fde6f7fad4387b0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429581B2

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