3,3,3-Trifluoropropanal → HCID 66802376, compound

HRID 341456

Reaction equation

HRID 341456 reaction equation
Cl.[CH3:2][N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:4]1[N:9]=[C:8]([NH2:10])[N:7]=[C:6]([C:11]2[N:15]=[C:14]([C@@H:16]3[CH2:20][CH2:19][CH2:18][NH:17]3)[O:13][N:12]=2)[N:5]=1.C([O-])(=O)C.[Na+].[F:32][C:33]([F:38])([F:37])[CH2:34][CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH3:2][N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:4]1[N:9]=[C:8]([NH2:10])[N:7]=[C:6]([C:11]2[N:15]=[C:14]([C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[CH2:35][CH2:34][C:33]([F:38])([F:37])[F:32])[O:13][N:12]=2)[N:5]=1

Participants

7

Reactant 4

HCID 680283,3,3-TrifluoropropanalHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 668025652-N-methyl-2-N-phenyl-6-{5-[(2S)-pyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamine hydrochloride

Product 1

HCID 66802376HCID 66802376, compoundYield 19.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-N-methyl-2-N-phenyl-6-{5-[(2S)-pyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamine hydrochloride (Example 438, 0.2 g, 0.535 mmol) in DCE (5 mL) was added sodium acetate (0.07 g, 0.8 mmol) and 3,3,3-trifluoropropanal (0.12 g, 1.070 mmol) and the mixture was stirred for 1 h at room temperature. Sodium triacetoxyborohydride (0.17 g, 0.8 mmol) was added and the reaction mixture was stirred for 2 h at room temperature. DCM was added and the mixture was washed with saturated aq. sodium bicarbonate, and then brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by FCC, eluting with 20-100% EtOAc in heptane to afford the title compound (0.045 g, 19%).

Workup

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. washthe mixture was washed with saturated aq. sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by FCC
  6. washeluting with 20-100% EtOAc in heptane

Sources & evidence

ORD record
ord-bcb1dbc97c884400b9c95defbcc88bec
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Linked notes

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