Triethylamine → HCID 86660482, compound

HRID 2175343Notes

Reaction equation

HRID 2175343 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([OH:13])=O.F[P-](F)(F)(F)(F)F.[N:21]1([O:30][C:31](N(C)C)=[N+](C)C)[C:25]2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CNOC>CN(C)C=O>[CH3:31][O:30][N:21]([CH3:25])[C:11]([C:3]1[NH:4][C:5]2[C:10]([C:2]=1[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:13]

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 27526383-Methyl-1H-indole-2-carboxylic acid

Product 1

HCID 86660482HCID 86660482, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methyl-1H-indole-2-carboxylic acid (from Matrix Scientific, 1.0 g, 5.7 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (4.3 g, 11 mmol) and triethylamine (4.0 mL, 28 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 10 minutes. N,O-Dimethylhydroxylamine hydrochloride (0.84 g, 8.6 mmol) was added and the resulting suspension was stirred at room temperature over the weekend. 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 0-30% EtOAc/hexane) to give the desired product (1.1 g, 88%). LCMS calculated for C12H15N2O2(M+H)+: m/z=219.1. Found: 219.1.

Workup

  1. stirringthe resulting suspension was stirred at room temperature over the weekend
  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 0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-8ab6e91903dc4615992b248e9f2dbf6b
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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