Dimethylamine → N-[2-(6-Chloro-4-dimethylaminomethyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

HRID 415750노트

반응식

HRID 415750 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=O)[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)([C:13]#[N:14])[CH3:12])[N:9]=2.[CH3:32][NH:33][CH3:34].[B][B][B][B][B][B][B][B][B][B]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:30][N:33]([CH3:34])[CH3:32])[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:19][CH:18]=1)([C:13]#[N:14])[CH3:12])[N:9]=2

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 59327634N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamideHCID 178419135HCID 178419135, 화합물

생성물 1

HCID 59327636N-[2-(6-Chloro-4-dimethylaminomethyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide수율 52%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide (0.18 g) in methanol (3 mL) was added a 2 molar methanolic solution of dimethylamine (0.24 mL). After one hour stirring at room temperature, decaborane was added (15 mg) and the mixture stirred one more hour before being concentrated under reduced pressure. The residue was purified by chromatography (SiO2, heptane/EA) to afford the title compound as a white solid (100 mg, 52%). Rf=0.2 (3:1 EA/heptane). MS (ES): M/Z [M+H]=481. 1H NMR: (400 MHz, CHLOROFORM-d): 1.81 (s, 3H), 2.31 (s, 6H), 3.75 (d, J=13.5 Hz, 1H), 3.92 (d, J=13.5 Hz, 1H), 5.12 (d, J=13.8 Hz, 1H), 5.52 (d, J=13.7 Hz, 1H), 7.32 (d, J=8.1 Hz, 2H), 7.36 (s, 1H), 7.81 (d, J=1.7 Hz, 1H) and 7.95 (br. d, J=8.7 Hz, 3H). 19F NMR (376 MHz, CHLOROFORM-d): −58.1 (s, 3F).

후처리

  1. stirringthe mixture stirred one more hour
  2. concentrationbefore being concentrated under reduced pressure
  3. customThe residue was purified by chromatography (SiO2, heptane/EA)

출처 및 근거

ORD 기록
ord-8c7f5038c0d247b5a793b801e6fb11a3
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088801B2

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