Bis(2-oxo-3-oxazolidinyl)phosphinic chloride → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-[2-(2-methoxy-ethoxy)-ethoxymethyl]-1H-pyrazole-3-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 604435ノート

反応式

HRID 604435 の反応式
[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]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:16][C:15]([C:27](O)=[O:28])=[N:14]3)[CH:8]=2)=[CH:4][CH:3]=1.Cl.[CH:31]([N:34]1[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35]1)([CH3:33])[CH3:32].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl.CCN(CC)CC>[CH:31]([N:34]1[CH2:39][CH2:38][CH:37]([NH:40][C:27]([C:15]2[CH:16]=[C:17]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[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:28])[CH2:36][CH2:35]1)([CH3:33])[CH3:32]

参加物

6

反応物 3

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 230334601-Isopropylpiperidin-4-amine hydrochlorideHCID 574744121-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-[2-(2-methoxy-ethoxy)-ethoxymethyl]-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 670409111-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-[2-(2-methoxy-ethoxy)-ethoxymethyl]-1H-pyrazole-3-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

To 60 mg 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-[2-(2-methoxy-ethoxy)-ethoxymethyl]-1H-pyrazole-3-carboxylic acid in 2 ml DCM and 0.1 ml NEt3, 30 mg 1-Isopropyl-piperidin-4-ylamine hydrochloride and 34 mg BOP-Cl were added at RT and the mixture was stirred for 16 h. The mixture 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. Yield: 19 mg MS (ES+): m/e=566, chloro pattern.

後処理

  1. concentrationThe mixture 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

出典と根拠

ORDレコード
ord-e6ab7f9913554415b437da4a93a843ee
出典データセット
uspto-grants-2011_03
特許番号
US07910606B2

反応ノート

読み込み中…