2-Pyridinemethanamine → HCID 59625603, compound

HRID 2192860Notes

Reaction equation

HRID 2192860 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].[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH2:44][NH2:45].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+]>[C:24]([C:21]1[N:20]=[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)[C:18]([C:16]([N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C@H:10]([C:35](=[O:36])[NH:45][CH2:44][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][N:38]=2)[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:17])=[CH:23][N:22]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 10989639Chloro-N,N,N',N'-tetramethylformamidinium HexafluorophosphateHCID 59625450HCID 59625450, compound

Product 1

HCID 59625603HCID 59625603, 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 (40 mg), 1-pyridin-2-ylmethanamine (157 μl) and diisopropylethylamine (330 μl) were dissolved in 1,2-dichloroethane (5 ml), chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (200 mg) was added, and the mixture was stirred at room temperature for 2 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 silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (1:9-1:0) was 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. washthe fraction eluted with ethyl acetate-hexane (1:9-1:0)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-b65a632e5d32410a8831d31dbf54f89d
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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