Triethylamine → HCID 11692046, compound

HRID 2387440Notes

Reaction equation

HRID 2387440 reaction equation
Cl.Cl.Cl.[CH3:4][C@H:5]1[CH2:10][N:9]([C:11]2([CH3:17])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:8][CH2:7][N:6]1[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=2)[CH2:20][CH2:19]1.[CH3:31][C:32]1[C:37]([C:38](O)=[O:39])=[C:36]([CH3:41])[N:35]=[CH:34][N:33]=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.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:31][C:32]1[C:37]([C:38]([N:14]2[CH2:13][CH2:12][C:11]([CH3:17])([N:9]3[CH2:8][CH2:7][N:6]([CH:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:28])[F:29])[CH:25]=5)[CH2:20][CH2:19]4)[C@@H:5]([CH3:4])[CH2:10]3)[CH2:16][CH2:15]2)=[O:39])=[C:36]([CH3:41])[N:35]=[CH:34][N:33]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 86601775HCID 86601775, compound

Product 1

HCID 11692046HCID 11692046, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S)-2-methyl-4-(4-methylpiperidin-4-yl)-1-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazine trihydrochloride (100 mg, 0.183 mmol), 4,6-dimethyl-pyrimidine-5-carboxylic acid (67 mg, 0.22 mmol) in DMF (5 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (97 mg, 0.22 mmol) followed by triethylamine (90 mg, 0.9 mmol). After being stirred at room temperature overnight, a solution of NaHCO3 in water was added. The resulting solution was extracted with EtOAc twice. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica (10-20% MeOH in EtOAc) afforded the title compound (60 mg) as an oil. MS calculated for C28H36F3N5O: (M+H)+ 516. found 516.2.

Workup

  1. extractionThe resulting solution was extracted with EtOAc twice
  2. washThe combined EtOAc layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e0ea9a8f2384a33a7e34ae90bc7d038
Source dataset
uspto-grants-2012_09
Patent number
US08268826B2

Reaction notes

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