Triethylamine → t-Butyl (2-{4-[2-(2-pyridin-3-yl-ethylcarbamoyl)vinyl]-benzoylamino}-phenyl)-carbamate

HRID 1180806노트

반응식

HRID 1180806 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([OH:28])=O)=[CH:20][CH:19]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH2:63][CH2:64][CH2:65][C:66]1[CH:67]=[N:68][CH:69]=[CH:70][CH:71]=1.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[N:68]1[CH:69]=[CH:70][CH:71]=[C:66]([CH2:65][CH2:64][NH:63][C:26]([CH:25]=[CH:24][C:21]2[CH:20]=[CH:19][C:18]([C:16]([NH:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:17])=[CH:23][CH:22]=2)=[O:28])[CH:67]=1

참가 물질

8

반응물 5

HCID 8471Triethylamine2회HCID 25517Ammonium ChlorideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 724798123-[4-(2-t-Butoxycarbonylamino-phenylcarbamoyl)-phenyl]-acrylic acid

생성물 1

HCID 86602772t-Butyl (2-{4-[2-(2-pyridin-3-yl-ethylcarbamoyl)vinyl]-benzoylamino}-phenyl)-carbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution at room temperature of compound XIII (80 mg, 0.21 mmol) in anhydrous DMF (3 ml) under nitrogen were added Et3N (35 μl, 0.25 mmol) and BOP reagent (102 mg, 0.23 mmol), respectively. After 30 min, a solution of 3-(2-aminoethyl)pyridine (51 mg, 0.42 mmol) or RXH (1.5–2.0 equiv.), Et3N (87 μl, 0.63 mmol) in anhydrous DMF (1 ml) was added dropwise. After 3–5 h, the reaction mixture was poured into a saturated aqueous solution of NH4Cl, and diluted with AcOEt. After separation, the organic layer was successively washed with sat NH4Cl, H2O and brine, dried over MgSO4, filtered, and concentrated to afford the title compound XIVf. It was used in the next step without further purification.

후처리

  1. waitAfter 3–5 h
  2. customAfter separation
  3. washthe organic layer was successively washed with sat NH4Cl, H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c7d3b6b3b7144f07ad1ca10650086a8c
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282608B2

반응 노트

불러오는 중…