Triethylamine → HCID 11697750, compound

HRID 851959Notes

Reaction equation

HRID 851959 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(CC)CC.[CH3:48][O:49][C:50]1[CH:55]=[CH:54][C:53]([C@@H:56]2[N:60]3[CH2:61][CH2:62][NH:63][CH2:64][C@@H:59]3[CH2:58][CH2:57]2)=[C:52]([CH3:65])[C:51]=1[CH3:66]>CC(N(C)C)=O.C1(C)C=CC=CC=1>[CH3:48][O:49][C:50]1[CH:55]=[CH:54][C:53]([C@@H:56]2[N:60]3[CH2:61][CH2:62][N:63]([C:7]([C:6]4[CH:5]=[N:4][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:11][CH:10]=4)=[O:9])[CH2:64][C@@H:59]3[CH2:58][CH2:57]2)=[C:52]([CH3:65])[C:51]=1[CH3:66]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27775516-(Trifluoromethyl)nicotinic acidHCID 58589329HCID 58589329, compound

Product 1

HCID 11697750HCID 11697750, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

6-Trifluoromethyl nicotinic acid (18.1 mg, 0.12 mmol), BOP (66.3 mg, 0.15 mmol), and Et3N (34.8 μL, 0.25 mmol) are added to a solution of (6R,8aS)-6-(4-methoxy-2,3-dimethylphenyl)-octahydro-pyrrolo[1,2-a]pyrazine (52.2 mg, 0.2 mmol) in anhydrous DMA (0.1 mL). The reaction mixture is stirred at 50° C. for 16 h, diluted with toluene, evaporated to dryness and the residue purified by filtration through an SCX cartridge, eluting with EtOAc-MeOH-NEt3 (10-1-1) to produce an oil (LC/MS: 434).

Workup

  1. customevaporated to dryness
  2. filtrationthe residue purified by filtration through an SCX cartridge
  3. washeluting with EtOAc-MeOH-NEt3 (10-1-1)
  4. customto produce an oil (LC/MS: 434)

Sources & evidence

ORD record
ord-3b4265a407234f0b86951306af0d0f87
Source dataset
uspto-grants-2007_08
Patent number
US07253168B2

Reaction notes

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