Dimethylamine → (4R)-1-(5-chloro-3-{5-[2-(dimethylamino)ethyl]-2-methoxyphenyl}-1-{[4-methoxy-2-(trifluoro methoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolin amide

HRID 1662757ノート

反応式

HRID 1662757 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][C:23]([F:26])([F:25])[F:24])(=[O:13])=[O:12])[C:6](=[O:27])[C:5]2([N:39]1[CH2:48][C@H:47]([OH:49])[CH2:46][C@H:40]1[C:41]([N:43]([CH3:45])[CH3:44])=[O:42])[C:28]1[CH:33]=[C:32]([CH2:34][CH:35]=O)[CH:31]=[CH:30][C:29]=1[O:37][CH3:38].[CH3:50][NH:51][CH3:52].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][C:23]([F:24])([F:25])[F:26])(=[O:12])=[O:13])[C:6](=[O:27])[C:5]2([N:39]1[CH2:48][C@H:47]([OH:49])[CH2:46][C@H:40]1[C:41]([N:43]([CH3:45])[CH3:44])=[O:42])[C:28]1[CH:33]=[C:32]([CH2:34][CH2:35][N:51]([CH3:52])[CH3:50])[CH:31]=[CH:30][C:29]=1[O:37][CH3:38]

参加物

8

反応物 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59867806HCID 59867806、化合物

生成物 1

HCID 59867773(4R)-1-(5-chloro-3-{5-[2-(dimethylamino)ethyl]-2-methoxyphenyl}-1-{[4-methoxy-2-(trifluoro methoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolin amide

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixed solution of 150 mg of the compound obtained in Example 218, a solution of 2 mol/L dimethylamine in THF (0.22 ml), 63 mg of acetic acid, 95 mg of sodium triacetoxy borohydride, in CHCl3 (1.5 ml) was stirred at room temperature for one hour. A saturated aqueous solution of NaHCO3 was added to the reaction solution, and the resulting mixture was extracted with CHCl3. The extract was dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. Purification was carried out by a preparative TLC plate (1 mm; mobile phase: CHCl3/MeOH=8/1; v/v) to obtain 75 mg of the title compound (colorless solid).

後処理

  1. extractionthe resulting mixture was extracted with CHCl3
  2. dry with materialThe extract was dried over Na2SO4
  3. customthe drying agent was separated by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customPurification

出典と根拠

ORDレコード
ord-d41da3e3cac54c9b8ebff1fc80a4f658
出典データセット
uspto-grants-2011_10
特許番号
US08030499B2

反応ノート

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