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

HRID 1180806ノート

反応式

HRID 1180806 の反応式
[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

参加物

8

反応物 5

HCID 8471Triethylamine2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c7d3b6b3b7144f07ad1ca10650086a8c
出典データセット
uspto-grants-2007_10
特許番号
US07282608B2

反応ノート

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