Triethylamine → HCID 117739540, compound

HRID 928584Notes

Reaction equation

HRID 928584 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:25]1([C:31]2[C:39]3[C:38]([N:40]4[CH2:45][CH2:44][CH2:43][CH:42]([C:46]([OH:48])=O)[CH2:41]4)=[N:37][CH:36]=[N:35][C:34]=3[S:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C.[O:56]1[CH2:61][CH2:60][N:59]([CH2:62][CH2:63][NH2:64])[CH2:58][CH2:57]1>C(#N)C>[O:56]1[CH2:61][CH2:60][N:59]([CH2:62][CH2:63][NH:64][C:46]([CH:42]2[CH2:43][CH2:44][CH2:45][N:40]([C:38]3[C:39]4[C:31]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[CH:32][S:33][C:34]=4[N:35]=[CH:36][N:37]=3)[CH2:41]2)=[O:48])[CH2:58][CH2:57]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 4571609HCID 4571609, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 117739540HCID 117739540, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.23099 g, 0.58928 mmol) was added to a suspension of 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidine-3-carboxylic acid (0.1 g, 0.29464 mmol) in acetonitrile (2 mL). Triethylamine (0.123 mL, 0.089443 g, 0.88391 mmol) and 2-morpholinoethanamine (0.0773 mL, 0.076718 g, 0.58928 mmol) were added and the mixture was stirred for 4 hr at room temperature. The solvent was evaporated and the residue was diluted with ethyl acetate (2 mL) and water (2 mL). The layers were separated and the aqueous was extracted with ethyl acetate (2×2 mL). The combined organic layers were washed with saturated aqueous sodium hydrogencarbonate (1×10 mL), dried (magnesium sulfate), filtered and evaporated to give a brown oil. Mass: 0.275 g. This was purified by prep HPLC (basic method 1). Fractions corresponding to the main peak were combined and evaporated to give a yellow oil. Yield=92 mg. LCMS [M+H]+=452; RT=2.89 min Other compounds prepared by Method K using the appropriate starting materials are listed in TABLE 1.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with ethyl acetate (2 mL) and water (2 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with ethyl acetate (2×2 mL)
  5. washThe combined organic layers were washed with saturated aqueous sodium hydrogencarbonate (1×10 mL)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customto give a brown oil
  10. customThis was purified by prep HPLC (basic method 1)
  11. customevaporated
  12. customto give a yellow oil

Sources & evidence

ORD record
ord-c25af47a26a74f8d8b963e2aeaddffef
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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