Sodium triacetoxyborohydride → 3-(2-{Bis-[4-(7-chloroquinolin-4-yl)butyl]amino}ethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide

HRID 1274407ノート

反応式

HRID 1274407 の反応式
[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[C:11]2[CH2:25][CH2:26][NH2:27])=[O:7])[CH:2]([CH3:4])[CH3:3].[Cl:32][C:33]1[CH:42]=[C:41]2[C:36]([C:37]([CH2:43][CH2:44][CH2:45][CH:46]=O)=[CH:38][CH:39]=[N:40]2)=[CH:35][CH:34]=1.C(O[BH-](O[C:58](=O)[CH3:59])OC(=O)C)(=O)C.[Na+]>>[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:11]2[CH2:25][CH2:26][N:27]([CH2:46][CH2:45][CH2:44][CH2:43][C:37]1[C:58]2[C:59](=[CH:42][C:33]([Cl:32])=[CH:34][CH:35]=2)[N:40]=[CH:39][CH:38]=1)[CH2:46][CH2:45][CH2:44][CH2:43][C:37]1[C:36]2[C:41](=[CH:42][C:33]([Cl:32])=[CH:34][CH:35]=2)[N:40]=[CH:39][CH:38]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]

参加物

4

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 221206734-(7-Chloroquinolin-4-yl)butyraldehydeHCID 537946513-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide

生成物 1

HCID 538582473-(2-{Bis-[4-(7-chloroquinolin-4-yl)butyl]amino}ethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide収率 23.8%

実験手順

To a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide (89 mg in 3.0 mL dry tetrahydrofuran) at 0° C. was added 50 mg 4-(7-chloroquinolin-4-yl)butyraldehyde and the mixture stirred for 10 minutes. At this time, 67.4 mg sodium triacetoxyborohydride were added and the mixture allowed to warm slowly to room temperature. After 5 hours, the reaction was quenched by the addition of brine and the mixture extracted with methylene chloride. The combined organics were dried over sodium sulfate and the concentrate purified by preparative tlc on silica gel (methylene chloride:methanol, 95:5) to give the title compound (21.8 mg).

後処理

  1. waitAfter 5 hours
  2. customthe reaction was quenched by the addition of brine
  3. extractionthe mixture extracted with methylene chloride
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. customthe concentrate purified by preparative tlc on silica gel (methylene chloride:methanol, 95:5)

出典と根拠

ORDレコード
ord-17f5b6d374ff43fcb4cec6c10174f08b
出典データセット
uspto-grants-2000_12
特許番号
US06156767

反応ノート

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