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

HRID 1274407Notes

Reaction equation

HRID 1274407 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-17f5b6d374ff43fcb4cec6c10174f08b
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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