Triethylamine → HCID 58368453, compound

HRID 1192539Notes

Reaction equation

HRID 1192539 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH3:18])=[N:10][C:9]=2[C:19]([OH:21])=O)[CH:5]=[CH:6][CH:7]=1.F[P-](F)(F)(F)(F)F.[N:29]1([O:38][C:39](N(C)C)=[N+](C)C)[C:33]2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CNOC>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH3:18])=[N:10][C:9]=2[C:19]([N:29]([O:38][CH3:39])[CH3:33])=[O:21])[CH:5]=[CH:6][CH:7]=1

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 58368670HCID 58368670, compound

Product 1

HCID 58368453HCID 58368453, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-fluorophenyl)-1-methylisoquinoline-3-carboxylic acid (400 mg, 1 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (700 mg, 1.8 mmol) and triethylamine (0.99 mL, 7.1 mmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature for 10 minutes. N,O-Dimethylhydroxylamine hydrochloride (180 mg, 1.8 mmol) was added and the resulting suspension was stirred at room temperature for 2 hours. The mixture was quenched with water and then extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, concentrated and the residue purified on silica gel (eluting with 0-80% ethyl acetate in hexane) to give the desired product (0.257 g, 60%). LCMS calculated for C19H18FN2O2 (M+H)+: m/z=325.1; Found: 325.1.

Workup

  1. stirringthe resulting suspension was stirred at room temperature for 2 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customthe residue purified on silica gel (eluting with 0-80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f2de98a517324c9f95f44b22d659ea49
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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