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

HRID 1180806Notes

Reaction equation

HRID 1180806 reaction equation
[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

Participants

8

Reactant 5

HCID 8471Triethylamine2×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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c7d3b6b3b7144f07ad1ca10650086a8c
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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