Triethylamine → HCID 45100906, compound

HRID 1096258Notes

Reaction equation

HRID 1096258 reaction equation
[OH:1][C@@H:2]1[CH2:9][N:8]([CH2:10][CH2:11][CH:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=3)[CH:18]([CH3:33])[C:17]2=[O:34])[C:13]([OH:15])=O)[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2.Cl.[CH3:36][NH:37][CH3:38].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[OH:1][C@@H:2]1[CH2:9][N:8]([CH2:10][CH2:11][CH:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=3)[CH:18]([CH3:33])[C:17]2=[O:34])[C:13]([N:37]([CH3:38])[CH3:36])=[O:15])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45100810HCID 45100810, compound

Product 1

HCID 45100906HCID 45100906, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-2-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-butyric acid (example 48; 40 mg, 82 μmol) in N,N-dimethylformamide (1.5 mL) was added dimethylamine hydrochloride (10 mg, 0.12 mmol), triethylamine (33 mg, 0.33 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (38 mg, 99 μmol), then after 1 h the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc) afforded the title compound (30 mg, 71%). Colorless oil, MS: 513.5 (M+H)+.

Workup

  1. customafter 1 h the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4a3325e233864d65a17dd1f6cf299591
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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