Triethylamine → HCID 56941483, compound

HRID 1529574Notes

Reaction equation

HRID 1529574 reaction equation
[CH:1]1([CH2:4][C:5]([OH:7])=O)[CH2:3][CH2:2]1.[O:8]([CH2:15][C:16]1[O:17][C:18]2[CH2:19][NH:20][CH2:21][CH2:22][C:23]=2[N:24]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.C([O-])(O)=O.[Na+]>[CH:1]1([CH2:4][C:5]([N:20]2[CH2:21][CH2:22][C:23]3[N:24]=[C:16]([CH2:15][O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[O:17][C:18]=3[CH2:19]2)=[O:7])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 138440Cyclopropaneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66609262HCID 66609262, compound

Product 1

HCID 56941483HCID 56941483, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Cyclopropylacetic acid (0.019 mL, 0.25 mmol) was added portionwise to a stirred solution of 4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (0.047 g, 0.21 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.078 g, 0.21 mmol), and triethylamine (0.043 mL, 0.31 mmol) in a mixture of THF (0.5 mL) and DMF (0.5 mL). The reaction mixture was stirred at room temperature for 15 hours and diluted with a saturated solution of NaHCO3. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-(cyclopropylacetyl)-4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (0.043 g, 67% yield) as an oil. C18H20N2O3. (mixture of rotamers 70:30) 1H NMR (400 MHz, CDCl3) δ ppm 0.10-0.27 (m, 2 H), 0.50-0.66 (m, 2 H), 0.98-1.16 (m, 1 H), 2.33 (d, J=6.7 Hz, 0.6 H), 2.38 (d, J=6.7 Hz, 1.4 H), 2.59-2.82 (m, 2 H), 3.72 (t, J=5.7 Hz, 1.4 H), 3.92 (t, J=5.7 Hz, 0.6 H), 4.52 (br. s, 0.6 H), 4.71 (br. s, 1.4 H), 5.11 (s, 1.4 H), 5.12 (s, 0.6 H), 6.81-7.01 (m, 1 H), 7.02 (d, J=7.9 Hz, 2 H), 7.27-7.46 (m, 2 H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50)
  6. customThe desired fractions were collected
  7. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-09a66ec1f63d492e955684e0ec7894cd
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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