Sodium hydride → 5-benzyloxy-4-methyl-9-(2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

HRID 1417971

반응식

HRID 1417971 반응식
[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[CH3:28])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=[O:6])[CH3:3].[H-].[Na+].[CH3:31][N:32]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33](=[O:36])[CH2:34]Br>O1CCCC1>[CH3:3][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[N:11]([CH2:34][C:33]([N:32]([CH3:31])[CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])[C:12]3[C:17]([C:9]=2[C:8]=1[CH3:28])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=[O:6])[CH3:1]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 10753531N-methyl-N-phenethyl-2-bromoacetamideHCID 541870645-benzyloxy-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

생성물 1

HCID 867538635-benzyloxy-4-methyl-9-(2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of 1.096 g of 5-benzyloxy-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester (2.93 mmol) in 2.9 ml of tetrahydrofuran is added to a suspension of 92.2 mg of sodium hydride (3.03 mmol; 80% in mineral oil) at 0° C. under nitrogen, and it is stirred for 10 minutes at 0° C. Then, 750 mg (2.93 mmol) of N-methyl-N-phenylethyl-2-bromoacetamide is added, and it is then stirred for 18 hours at 24° C. It is filtered off on Celite, the filtrate is concentrated by evaporation in a vacuum, and the crude product that is thus obtained is purified on a silica gel column with hexane/0-100% ethyl acetate. In this way, 1.24 g of 5-benzyloxy-4-methyl-9-(2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is obtained as an amorphous, yellowish-colored solid with a melting point of 69°-74° C.

후처리

  1. stirringit is then stirred for 18 hours at 24° C
  2. filtrationIt is filtered off on Celite
  3. concentrationthe filtrate is concentrated by evaporation in a vacuum
  4. customthe crude product that is thus obtained
  5. customis purified on a silica gel column with hexane/0-100% ethyl acetate

출처 및 근거

ORD 기록
ord-1bc8f937dc24454dbc755016e4c1448a
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05880126

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