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Triethylamine → HCID 11692046, compound

HRID 2244901
Notes
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Reaction equation

HRID 2244901 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 11692046
HCID 11692046, compound
Yield 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-dimethylpyrimidine-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-22f72cdaa83e43f29f06ece10a182f32
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07678798B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes