Benzylamine → HCID 59625338, compound

HRID 2192859Notes

Reaction equation

HRID 2192859 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([C:35](O)=[O:36])[N:11]([C:16]([C:18]1[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[N:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[N:22][CH:23]=1)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.ClC(N(C)C)=[N+](C)C>ClCCCl.C(=O)([O-])O.[Na+]>[CH2:38]([NH:45][C:35](=[O:36])[C@@H:10]([N:11]([C:16]([C:18]1[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[N:20][C:21]([C:24]([CH3:25])([CH3:27])[CH3:26])=[N:22][CH:23]=1)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 10989639Chloro-N,N,N',N'-tetramethylformamidinium HexafluorophosphateHCID 59625450HCID 59625450, compound

Product 1

HCID 59625338HCID 59625338, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-[(tert-Butoxycarbonyl)amino]-N-({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)-N-(2-methylpropyl)-L-alanine (27 mg), benzylamine (200 μl) and diisopropylethylamine (300 μl) were dissolved in 1,2-dichloroethane (5 ml), chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (100 mg) was added, and the mixture was stirred at room temperature for 3.5 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and fractions eluted with water-acetonitrile (9:1) to acetonitrile were collected. The mixture was basified (pH 10) with saturated aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the object compound (19 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. washeluted with water-acetonitrile (9:1) to acetonitrile
  5. customwere collected
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2054e378a98647b8a392c2780b8771a0
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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