Tetrahydrofuran → 6-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

HRID 1417960Notes

Reaction equation

HRID 1417960 reaction equation
[CH3:1][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[CH:16][C:15]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:14][CH:13]=3)=[O:6])[CH3:3].[H-].[Na+].[CH3:33][N:34]([CH:43](Br)[C:44](N)=O)[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[O:48]1CCCC1>>[CH3:3][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[N:11]([CH2:44][C:43]([N:34]([CH3:33])[CH2:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:48])[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[CH:16][C:15]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:14][CH:13]=3)=[O:6])[CH3:1]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 65914AbecarnilHCID 676962902-[N-methyl-N-(2-phenylethyl)-amino]-2-bromoacetamide

Product 1

HCID 98083526-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

Procedure

998 mg of 6-benzyloxy-4-methoxymethyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-1-methylethyl-ester (2.4 mmol) is introduced into 10 ml of dry tetrahydrofuran and deprotonated at 0° C. with 72 mg of sodium hydride (80% suspension in oil) (2.4 mmol). Then, it is stirred for 20 minutes at room temperature, mixed with 630 mg of 2-[N-methyl-N-(2-phenylethyl)-amino]-2-bromoacetamide (2.4 mmol)--dissolved in 10 ml of tetrahydrofuran--stirred for another 5 hours at room temperature, filtered on diatomaceous earth, and then the solvent is drawn off in a vacuum. The crude product that is obtained is recrystallized from dichloromethane/diethyl ether, and 1.22 g of 6-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)amino]-2-oxoethyl}-9H-pyrido-[3,4-b]indole-3-carboxylic acid-(1-methyl-ethyl)-ester is obtained.

Workup

  1. stirringstirred for another 5 hours at room temperature
  2. filtrationfiltered on diatomaceous earth
  3. customThe crude product that is obtained
  4. customis recrystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-6c72901aec0041c1927b42cd96f93b3b
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

Loading…