Triethylamine → 2-Ethynyl-3'',4''-dimethoxy-biphenyl-4-carboxylic acid (1-methyl-4-pyridin-3-yl-butyl)-amide

HRID 2073300노트

반응식

HRID 2073300 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[CH:13][C:12]=2[C:20]#[CH:21])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:46][C@@H:47]([NH2:57])[CH2:48][CH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1>CN(C)C=O.C(OCC)(=O)C>[C:20]([C:12]1[CH:13]=[C:14]([C:17]([NH:57][C@H:47]([CH3:46])[CH2:48][CH2:49][CH2:50][C:51]2[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=2)=[O:18])[CH:15]=[CH:16][C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)#[CH:21]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11062727(R)-2-Amino-5-(3-pyridyl)pentaneHCID 145701343',4'-Dimethoxy-2-ethynyl[1,1'-biphenyl]-4-carboxylic acid

생성물 1

HCID 145701032-Ethynyl-3'',4''-dimethoxy-biphenyl-4-carboxylic acid (1-methyl-4-pyridin-3-yl-butyl)-amide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 459 mg of 3',4'-dimethoxy-2-ethynyl[1,1'-biphenyl]-4-carboxylic acid in 8 mL of dimethylformamide was cooled in an ice bath and treated with 0.25 mL of triethylamine and 0.38 mL of diphenylphosphoryl azide. After 1 hour. 0.3 mL of (R)alpha-methyl-3-pyridinebutanamine was added and the reaction mixture was allowed to warm to room temperature over 48 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was chromatographed over 50 g of silica gel eluting with ethyl acetate and the product was crystallized from ethyl acetate-hexane to give 576 mg of (R)-2-Ethynyl-3',4'-dimethoxy-N-[1-methyl-4-(3-pyridinyl)butyl][1.1'-biphenyl]-4-carboxamide, mp 135°-137° C.

후처리

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed over 50 g of silica gel eluting with ethyl acetate
  5. customthe product was crystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-ce066783a42247559d200bdd11fbcd1e
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04916145

반응 노트

불러오는 중…