Triethylamine → HCID 66616333, compound

HRID 1917276Notes

Reaction equation

HRID 1917276 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH2:13][N:12]([C:14](=[O:16])[CH3:15])[CH2:11][CH2:10][C:9]=2N2CCCCC2)=O)=[CH:4][CH:3]=1.CCN(CC)CC.Cl.[CH3:33][CH:34]([CH3:38])[C:35](=[NH:37])[NH2:36]>C(O)(CC)(C)C>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]2[C:8]3[CH2:13][N:12]([C:14](=[O:16])[CH3:15])[CH2:11][CH2:10][C:9]=3[N:37]=[C:35]([CH:34]([CH3:38])[CH3:33])[N:36]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27820532-Methylpropanimidamide hydrochlorideHCID 666163811-[5'-(4-fluoro-benzoyl)-3,4,5,6,3',6'-hexahydro-2H,2'H-[1,4']bipyridinyl-1'-yl]-ethanone

Product 1

HCID 66616333HCID 66616333, compound

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

A solution of crude 1-[5′-(4-fluoro-benzoyl)-3,4,5,6,3′,6′-hexahydro-2H,2′H-[1,4′]bipyridinyl-1′-yl]-ethanone in t-amyl alcohol (1.5 L) was treated with Et3N (108 mL, 0.78 mol) and 2-methyl propanimidamide hydrochloride (82.6 g, 0.67 mol). The reaction mixture was heated at reflux for 16 h and then was cooled to rt. The mixture was concentrated, and the residue was diluted with water (2 L) and extracted with EtOAc (2×). The combined organic layers were dried (MgSO4) and concentrated to afford the crude title compound, which was used in next reaction without further purification. HPLC: RT=8.11 min. MS (ESI): exact mass calcd. for C18H20FN3O, 313.16; m/z found, 314.0 [M+H]+. 1H NMR (CDCl3; mixture of rotamers): 7.60-7.50 (m, 2H), 7.24-7.12 (m, 2H), 4.71 (s, 1.4H), 4.56 (s, 0.6H), 3.93 (t, J=6.2, 0.6H), 3.80 (t, J=6.2, 1.4H), 3.18 (sept, J=6.8, 1H), 3.07 (t, J=6.2, 1.4H), 3.02 (t, J=6.2, 0.6H), 2.15 (s, 2.1H), 2.00 (s, 0.9H), 1.34 (d, J=6.8, 6H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationThe mixture was concentrated
  4. additionthe residue was diluted with water (2 L)
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1d74c00b0e804589b79dd14da067d2d4
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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