(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮 → 4-Methoxy-N,2,6-trimethyl-N-[(5-{[4-(3-pyrrolidin-1-ylpropyl)piperazin-1-yl]carbonyl}-1,3,4-oxadiazol-2-yl)methyl]benzenesulfonamide

HRID 469089

反应方程式

HRID 469089 反应方程式
[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28]([N:31]([CH2:33][C:34]2[O:38][C:37]([C:39](OC)=[O:40])=[N:36][N:35]=2)[CH3:32])(=[O:30])=[O:29])=[C:23]([CH3:43])[CH:22]=1.CO>C1COCC1>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28]([N:31]([CH3:32])[CH2:33][C:34]2[O:38][C:37]([C:39]([N:12]3[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH2:14][CH2:13]3)=[O:40])=[N:36][N:35]=2)(=[O:30])=[O:29])=[C:23]([CH3:43])[CH:22]=1

参与物

6

反应物 4

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮HCID 27372521-(3-吡咯烷丙基)哌嗪HCID 16682925三甲基铝HCID 67217606Methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate

产物 1

HCID 583932084-Methoxy-N,2,6-trimethyl-N-[(5-{[4-(3-pyrrolidin-1-ylpropyl)piperazin-1-yl]carbonyl}-1,3,4-oxadiazol-2-yl)methyl]benzenesulfonamide

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
-40 °C

实验过程

1-(3-Pyrrolidin-1-ylpropyl)piperazine (128 mg, 1.65 mmol) was dissolved in THF (5 mL) and the resulting solution was cooled to −40° C. prior to the addition of trimethylaluminium (2 M in toluene, 0.59 mL). The reaction was stirred for 15 min at −40° C. and a solution of methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (200 mg, 0.54 mmol) in THF (5 mL) was added dropwise. The reaction was stirred at ambient temperature for 18 h and MeOH (5 mL) was added. The solvents were removed in vacuo and the resulting residue was purified by FCC, eluting with 0-2% MeOH in DCM to afford the title compound as a pale yellow semi solid.

后处理

  1. stirringThe reaction was stirred at ambient temperature for 18 h
  2. customThe solvents were removed in vacuo
  3. customthe resulting residue was purified by FCC
  4. washeluting with 0-2% MeOH in DCM

来源与证据

ORD记录
ord-2281eb1867284a5ca0e93fe9947c5ae1
来源数据集
uspto-grants-2014_01
专利号
US08623859B2

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