Triethylamine → HCID 86660481, compound

HRID 2175337Notes

Reaction equation

HRID 2175337 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([OH:12])=O.F[P-](F)(F)(F)(F)F.[N:20]1([O:29][C:30](N(C)C)=[N+](C)C)[C:24]2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CNOC>CN(C)C=O>[CH3:30][O:29][N:20]([CH3:24])[C:10]([C:2]1[NH:1][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1)=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71446231H-Pyrrolo[2,3-b]pyridine-2-carboxylic Acid

Product 1

HCID 86660481HCID 86660481, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (from MolBridge, 1.0 g, 6.2 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.0 g, 8.0 mmol) and triethylamine (4.3 mL, 31 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 10 minutes. N,O-dimethylhydroxylamine hydrochloride (0.78 g, 8.0 mmol) was added and the resulting suspension was stirred at room temperature overnight. The mixture was quenched with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-65% EtOAc/hexane) to give the desired product (1.0 g, 79%). LCMS calculated for C10H12N3O2(M+H)+: m/z=206.1. Found: 206.1.

Workup

  1. stirringthe resulting suspension was stirred at room temperature overnight
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel (eluting with 0-65% EtOAc/hexane)

Sources & evidence

ORD record
ord-41d226147c244c48bc81e91e3e19304f
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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