Triethylamine → HCID 58388035, compound

HRID 2080226Notes

Reaction equation

HRID 2080226 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]2=[CH:4][C:3]=1[C:11]([OH:13])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[O:48]([C:55]1[S:59][C:58]([CH2:60][NH2:61])=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C)C=O.[Cl-].[Na+].O>[O:48]([C:55]1[S:59][C:58]([CH2:60][NH:61][C:11]([C:3]2[CH:4]=[C:5]3[CH2:10][CH2:9][CH2:8][C:6]3=[N:7][C:2]=2[NH2:1])=[O:13])=[CH:57][CH:56]=1)[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23130515C-(5-Phenoxy thiophen-2-yl)methylamineHCID 54595024115271-79-9

Product 1

HCID 58388035HCID 58388035, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Amino-6,7-dihydro-5H-cyclopenta[b]pyridine-3carboxylic acid described in Preparation Example C-5 (100 mg, 0.56 mmol), triethylamine (0.188 mL, 1.35 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (298 mg, 0.67 mmol) were dissolved in N,N-dimethylformamide (3 mL), C-(5-phenoxy-thiophen-2-yl)-methylamine described in Preparation Example 26 (138 mg, 0.67 mmol) was added, followed by stirring for 15 hours 20 minutes at room temperature. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), and the title compound (77 mg, 0.21 mmol, 38%) was obtained.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-56dd8dd3d0ea41dcb20e96500f2ddd6e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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