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

HRID 1274407노트

반응식

HRID 1274407 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-17f5b6d374ff43fcb4cec6c10174f08b
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156767

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