Methanesulfonyl chloride → 1-(2,2-Dimethylpropyl)-3-methyl-5-[2-(methylsulfonyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 629876ノート

反応式

HRID 629876 の反応式
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH2:14][CH:15]4[CH2:19][NH:18][CH2:17][CH:16]4[CH:20]=3)=[CH:10][CH:11]=2)[N:6]([CH3:21])[C:5]1=[O:22].CCN(C(C)C)C(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH2:14][CH:15]4[CH2:19][N:18]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:17][CH:16]4[CH:20]=3)=[CH:10][CH:11]=2)[N:6]([CH3:21])[C:5]1=[O:22]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 711361941-(2,2-Dimethylpropyl)-5-(1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

生成物 1

HCID 711367471-(2,2-Dimethylpropyl)-3-methyl-5-[2-(methylsulfonyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-(2,2-Dimethylpropyl)-5-(1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (84, 100 mg, 0.30 mmol, 1.0 equiv), and DIPEA (0.16 mL, 0.91 mmol, 3.0 equiv) were added to anhydrous methylene chloride (3 mL). Stirred for 5 min and methanesulfonyl chloride (26.3 μL, 0.33 mmol, 1.1 equiv) was added. After stirring for 10 min at room temperature, LCMS showed consumption of starting material. Purification by reverse-phase HPLC (20-100% CH3CN:0.1% TFA in H2O) provided 10-1 as a pale yellow oil. MS m/z (M+H): calculated=405.1957; observed=405.1969.

後処理

  1. stirringAfter stirring for 10 min at room temperature
  2. customconsumption of starting material
  3. customPurification by reverse-phase HPLC (20-100% CH3CN:0.1% TFA in H2O)

出典と根拠

ORDレコード
ord-5ef43f52b47f47cf8385fc725b1dcf45
出典データセット
uspto-grants-2016_04
特許番号
US09315518B2

反応ノート

読み込み中…