Methanesulfonyl chloride → 4-((2-(Ethylamino)-6-methoxyquinolin-3-yl)methyl)-6,7-dimethoxy-1-(methylsulfonamidomethyl)isoquinolin-3-yl methanesulfonate

HRID 1620246ノート

反応式

HRID 1620246 の反応式
C([O:4][C:5]1[N:6]=[C:7]([CH2:35][NH:36]C(=O)C)[C:8]2[C:13]([C:14]=1[CH2:15][C:16]1[C:17]([NH:28][CH2:29][CH3:30])=[N:18][C:19]3[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][CH3:27])=[CH:21][CH:20]=3)=[CH:12][C:11]([O:31][CH3:32])=[C:10]([O:33][CH3:34])[CH:9]=2)(=O)C.CC(N(C(C)C)CC1C=CC=CC=1)C.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.[CH3:72][S:73](Cl)(=[O:75])=[O:74]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:72][S:73]([O:4][C:5]1[N:6]=[C:7]([CH2:35][NH:36][S:73]([CH3:72])(=[O:75])=[O:74])[C:8]2[C:13]([C:14]=1[CH2:15][C:16]1[C:17]([NH:28][CH2:29][CH3:30])=[N:18][C:19]3[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][CH3:27])=[CH:21][CH:20]=3)=[CH:12][C:11]([O:31][CH3:32])=[C:10]([O:33][CH3:34])[CH:9]=2)(=[O:75])=[O:74]

参加物

6

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 16212447N-benzyl-N-propan-2-ylpropan-2-amine;1,4-bis(ethenyl)benzene;styreneHCID 601638771-(Acetamidomethyl)-4-((2-(ethylamino)-6-methoxyquinolin-3-yl)methyl)-6,7-dimethoxyisoquinolin-3-yl acetate

生成物 1

HCID 866698234-((2-(Ethylamino)-6-methoxyquinolin-3-yl)methyl)-6,7-dimethoxy-1-(methylsulfonamidomethyl)isoquinolin-3-yl methanesulfonate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

The other portion of the residue CCH 42006-2 (see preparation of compound 56) was transferred in a 5 mL microwave vial equipped with a magnetic stirrer before addition of diisopropylaminomethyl-polystyrene resin (3 mmol/g, 86 mg, 258 μmol), DMAP (2 mg, 16 μmol) and methanesulfonyl chloride (25 μL, 323 μmol) and the reaction mixture was stirred for 20 min at 100° C. under microwave irradiation. After cooling to RT, the mixture was diluted with CH2Cl2 (30 mL), filtered through cotton wool, then washed with brine (5 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100) gave 4-((2-(ethylamino)-6-methoxyquinolin-3-yl)methyl)-6,7-dimethoxy-1-(methylsulfonamidomethyl)isoquinolin-3-yl methanesulfonate as a pale yellow solid.

後処理

  1. temperatureAfter cooling to RT
  2. filtrationfiltered through cotton wool
  3. washwashed with brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100)

出典と根拠

ORDレコード
ord-dd6444e138784ff7839154d24e1a8d5e
出典データセット
uspto-grants-2014_07
特許番号
US08772316B2

反応ノート

読み込み中…