Triethylamine → HCID 69748478, compound

HRID 497485Notes

Reaction equation

HRID 497485 reaction equation
Cl.Cl.[F:3][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C@H:16]3[C@H:21]([NH2:22])[CH2:20][CH2:19][CH2:18][O:17]3)[CH2:10]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:32]([C:35]1[CH:36]=[C:37]([N:41]=[C:42]=[O:43])[CH:38]=[CH:39][CH:40]=1)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([C:35]1[CH:36]=[C:37]([NH:41][C:42]([NH:22][C@@H:21]2[CH2:20][CH2:19][CH2:18][O:17][C@H:16]2[CH2:15][N:11]2[CH2:12][CH2:13][CH2:14][C@@H:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:24][CH:23]=3)[CH2:10]2)=[O:43])[CH:38]=[CH:39][CH:40]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3127181-(3-Isocyanatophenyl)ethan-1-oneHCID 21362440HCID 21362440, compound

Product 1

HCID 69748478HCID 69748478, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S,3R)-2-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-tetrahydro-pyran-3-ylamine dihydrochloride (16 mg, 0.043 mmol—prepared according to Part I) and excess triethylamine (100 μL, 0.719 mmol) in methylene chloride (1 mL) was added 3-acetylphenyl isocyanate (6.9 mg, 0.043) dissolved in methylene chloride (1 mL). The resulting yellow solution was shaken vigorously for 20 sec, and allowed to stand at 23° C. for 10 min. The solution was then concentrated in vacuo, and the resulting residue was purified by flash chromatography (5% methanol in methylene chloride) to yield the desired urea (13 mg, 65%) as a pale yellow oil. MS (ESI), m+/z: (M+H)+=468.3.

Workup

  1. waitto stand at 23° C. for 10 min
  2. concentrationThe solution was then concentrated in vacuo
  3. customthe resulting residue was purified by flash chromatography (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-389d7dc78e234b1fb771daf90c85940e
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

Loading…