Ammonia → HCID 86586745, compound

HRID 2088197Notes

Reaction equation

HRID 2088197 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16](O)=[O:17])[CH2:15][C@@:9]1([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:10]([O:19][C@H:20]([C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=1)[CH3:21])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:44](CC)CC)C.Cl.CN(C)CCCN=C=NCC.N.O1CCOCC1>CN(C)C1C=CN=CC=1.ClCCl.O>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]([NH2:44])=[O:17])[CH2:15][C@@:9]1([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:10]([O:19][C@H:20]([C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=1)[CH3:21])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86586743HCID 86586743, compound

Product 1

HCID 86586745HCID 86586745, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid (Example 130; 4.82 g, 6.99 mmol), triethylamine (2.93 ml, 20.97 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (2.68 g, 13.98 mmol), 4-dimethylaminopyridine (10 mg), and ammonia in dioxane (41.94 ml, 20.97 mmol, 0.5M solution) were combined in dichloromethane (40 ml) and stirred in a sealed flask for 2 hours at room temperature. The reaction mixture was then diluted with water and the organics removed and the aqueous further extracted with dichloromethane (×2). All organics were combined, dried (MgSO4) and concentrated in vacuo to give a brown oil which was purified by flash column chromatography [3% methanol in dichloromethane] to give the title compound as a cream-coloured solid (1.76 g, 60%).

Workup

  1. customthe organics removed
  2. extractionthe aqueous further extracted with dichloromethane (×2)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil which
  6. customwas purified by flash column chromatography [3% methanol in dichloromethane]

Sources & evidence

ORD record
ord-a6cd61e7c9c5495ab4652f32778eaff5
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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