Triethylamine → HCID 68807152, compound

HRID 411282

Reaction equation

HRID 411282 reaction equation
CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH2:28][CH:29]1[CH2:36][CH:35]2[CH2:37][C:31]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([OH:54])[CH:49]=3)([CH:32]([CH3:47])[CH2:33][N:34]2[CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:30]1.Cl.[CH3:56][N:57]([CH3:64])[CH2:58][CH2:59][CH2:60][C:61](O)=[O:62].C(N(CC)CC)C>C1COCC1.CCOCC>[CH3:56][N:57]([CH3:64])[CH2:58][CH2:59][CH2:60][C:61]([NH:28][C@H:29]1[CH2:36][C@H:35]2[CH2:37][C@:31]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([OH:54])[CH:49]=3)([C@H:32]([CH3:47])[CH2:33][N:34]2[CH2:38][CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:30]1)=[O:62]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 18540869HCID 18540869, compound

Product 1

HCID 68807152HCID 68807152, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

BOP reagent (27 mg, 0.060 mmol) was added to a solution of (+)-7-amino-4-methyl-5-(3 -hydroxyphenyl)-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonane (23, 20 mg, 0.055 mmol), 4-(dimethylamino)butyric acid hydrochloride (18 mg, 0.11 mmol) and triethylamine (0.038 mL, 0.27 mmol) in dry THF (5 mL). The reaction mixture was stirred under N2 at room temperature for 4 h. The mixture was diluted with Et2O (20 mL), washed with saturated NaHCO3, followed by water, organic layer collected, dried (Na2SO4) and solvent removed under reduced pressure yielding crude product. This was purified by flash chromatography (33% (80% CHCl3:18% CH3OH:2% NH4OH) in CHCl3) to afford 4-(dimethylamino)-N-[(1R,4S,5S,7R)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]butanamide (13) (23 mg, 89%) as an off-white foam. 1H-NMR (CDCl3) δ7.28-7.09 (m, 6H), 6.89 (d, 1H, J=7.0 Hz), 6.64-6.59 (m, 3H), 6.31 (m, 1H), 4.65 (br., 1H), 3.16 (br., 1H), 3.02 (d, 1H, J=7.8 Hz), 2.69-2.14 (m, 16H), 1.91 (m, 1H), 1.86-1.75 (m, 4H), 1.58 (m 1H), 1.36-0.83 (m, 3H), 0.71 (d, 3H, J=6.5 Hz); LRMS (ES) m/z 478.7 (M+H)+.

Workup

  1. washwashed with saturated NaHCO3
  2. customcollected
  3. dry with materialdried (Na2SO4) and solvent
  4. customremoved under reduced pressure
  5. customyielding crude product
  6. customThis was purified by flash chromatography (33% (80% CHCl3:18% CH3OH:2% NH4OH) in CHCl3)

Sources & evidence

ORD record
ord-e78ab4ca0d1b4f7f9a608a1633d02ea5
Source dataset
uspto-grants-2003_05
Patent number
US06559159B2

Linked notes

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