Triethylamine → HCID 23130636, compound

HRID 2080171Notes

Reaction equation

HRID 2080171 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C([N:14]([CH2:17][CH3:18])CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:30]2[CH:31]=C[CH:33]=[CH:34][C:29]=2N=N1.[F:46][C:47]1[CH:62]=[CH:61][CH:60]=[CH:59][C:48]=1[CH2:49][O:50]NCC1C=CC=CC=1>[Cl-].[Na+].O.CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:14][CH2:17][C:18]1[CH:33]=[CH:34][C:29]([O:50][CH2:49][C:48]2[CH:59]=[CH:60][CH:61]=[CH:62][C:47]=2[F:46])=[CH:30][CH:31]=1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 189772452,6-Diaminonicotinic acidHCID 86761305HCID 86761305, compound

Product 1

HCID 23130636HCID 23130636, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (200 mg, 1.3 mmol), triethylamine (0.54 mL, 3.87 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (862 mg, 1.95 mmol) were added to N,N-dimethylformamide (20 mL), and the solution was stirred at room temperature for 20 minutes. Next, 4 (2-fluoro-benzyloxy)-benzylamine described in Preparation Example 154 (453 mg, 1.96 mmol) was added thereto, and the solution was stirred at room temperature for 14 hours. After the reaction was completed, the reaction solution was poured into brine, the solution was extracted with ethyl acetate, the fractionated organic layer was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was subjected to silica gel column chromatography, eluted with solvent (ethyl acetate) and the title compound (147 mg, 0.40 mmol, 31%) was obtained.

Workup

  1. additionwas added
  2. stirringthe solution was stirred at room temperature for 14 hours
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialthe fractionated organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with solvent (ethyl acetate)

Sources & evidence

ORD record
ord-518d28c1d5f74d438c1df55cbe9b548d
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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