Triethylamine → HCID 58080690, compound

HRID 2170065Notes

Reaction equation

HRID 2170065 reaction equation
CC(CC(C1C(O)=[CH:11][C:10](O)=[C:9]([CH2:15][CH:16]=C(C)C)[C:8]=1[O-:20])=O)C.CN(C(ON1N=[N:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:45]([N:47](CC)CC)C.[NH2:52][CH2:53][C:54]1[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=1.[CH3:60][N:61]([CH3:65])[C:62](=[O:64])[CH3:63]>[NH4+].[Cl-]>[C:45]([C:63]1[C:62](=[O:64])[N:61]([CH3:65])[C:60]2[C:32]([C:31]=1[N:36]1[CH2:11][CH2:10][CH:9]([C:8]([NH:52][CH2:53][C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)=[O:20])[CH2:15][CH2:16]1)=[CH:33][CH:34]=[CH:35][CH:30]=2)#[N:47]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 773174-PyridinemethanamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252006104-Prenylphlorisovalerophenone

Product 1

HCID 58080690HCID 58080690, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

Compound X (0.10 g, 1.0 eq) was taken up in N,N-dimethylacetamide (2 ml) then treated with HBTU (0.16 g, 1.3 eq) and triethylamine (49 uL, 1.1 eq). After 10 minutes at room temperature, commercially available 4-aminomethylpyridine (37.8 mg, 1.1 eq) was added. The reaction stirred at room temperature for 15 h before diluting with saturated NH4Cl aq. to quench. The mixture was extracted with ethylacetate (3×-5 ml). The organics were washed with water (3×-5 mL), and brine (2×-5 mL) then dried over Na2SO4 and concentrated for crude material. The residue was loaded on silica gel (24 g) and eluted with a gradient of 0-10 MeOH/DCM for 20 CVs. Late fractions afforded the desired product as a lightly tan solid (5.1 mg, 3.8% yield; calc M+H 402, obs M+H 402).

Workup

  1. customto quench
  2. extractionThe mixture was extracted with ethylacetate (3×-5 ml)
  3. washThe organics were washed with water (3×-5 mL), and brine (2×-5 mL)
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated for crude material
  6. washeluted with a gradient of 0-10 MeOH/DCM for 20 CVs

Sources & evidence

ORD record
ord-341fa67e945c464e90b66e02f21ebb18
Source dataset
uspto-grants-2015_06
Patent number
US09050334B2

Reaction notes

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