Triethylamine → HCID 86588314, compound

HRID 481069Notes

Reaction equation

HRID 481069 reaction equation
Br.[N:2]1[CH:3]=[CH:4][N:5]2[C:13]=1[C:12]1[C:11]([C:14]([OH:16])=O)=[CH:10][NH:9][C:8]=1[CH2:7][CH2:6]2.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[F:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1>O.CN(C)C=O>[F:48][C:49]1[CH:55]=[CH:54][C:52]([NH:53][C:14]([C:11]2[C:12]3[C:13]4[N:5]([CH:4]=[CH:3][N:2]=4)[CH2:6][CH2:7][C:8]=3[NH:9][CH:10]=2)=[O:16])=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69735974HCID 69735974, compound

Product 1

HCID 86588314HCID 86588314, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid hydrobromide (58 mg), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (181 mg), triethylamine (0.07 mL), 4-fluoroaniline (30 mg), and N,N-dimethylformamide (4 mL) is heated at 400 for 18 hours. The mixture is cooled to room temperature, treated with water (15 mL), and extracted with ethyl acetate (3×50 mL). The combined organic layers are washed with water (2×15 mL) and brine (1×15 mL), dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by preparative thin layer chromatography on silica gel, eluting with 5% methanol in dichloromethane, to give 5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid (4-fluorophenyl)amide, pale brown solid, 18 mg: LRMS calcd 296.30, found [M+H] 297.2.

Workup

  1. temperatureis heated at 400 for 18 hours
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers are washed with water (2×15 mL) and brine (1×15 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by preparative thin layer chromatography on silica gel
  7. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-03760b616cb74170b94efc15b7b4ad01
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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