Triethylamine → HCID 19601665, compound

HRID 610648Notes

Reaction equation

HRID 610648 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([C:18]([OH:20])=O)[N:9]=2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:28]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:32]2C=CC=CC=2N=N1.Cl.CN.CCN(CC)CC>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([C:18]([NH:28][CH3:32])=[O:20])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6364545Methylamine hydrochlorideHCID 19601660HCID 19601660, compound

Product 1

HCID 19601665HCID 19601665, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-iodophenyl)-3-isoquinolinecarboxylic acid (0.2073 g, 0.55 mmol), BOP (0.2447 g, 0.55 mmol), Methylamine hydrochloride (0.096 g, 1.42 mmol), and Et3N (0.25 mL, 1.80 mmol) in DMF (8 mL) was stirred under Ar at room temperature. After stirring for 1 h , additional Et3N (0.2 ml,) was added in one portion. The mixture was stirred under Ar for 7 h, then quenched by adding H2O (8 mL). The resulting mixture was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried (Na2SO4), then filtered. The filtrate was concentrated in vacuo. The residue was purified on column chromatography (SiO2, 35% ethyl acetate in hexane, 0.1% Et3N), thereby affording the title compound as a white solid (0.1724, 81%). mp 163-164 ° C. 1H NMR (CDCl3) d 3.07, 3.09 (two s, total 3 H, N-methyl), 7.46 (d, J=8.4 Hz, 2 H, aromatic), 7.64 (t, J=7.2 Hz, 1 H, aromatic), 7.77 (t, J=6.9 Hz, 1 H, aromatic), 7.92 (d, J=8.4 Hz, 2 H, aromatic), 8.07 (t, J=7.8 Hz, 2 H, aromatic), 8.24 (br s, 1 H, NH), 8.02 (s, 1 H, aromatic). 13C NMR (CDC13) d 26.05 (q,N-methyl), 95.14 (s, C--I), 119.54 (d, aromatic), 127.02 (d, aromatic), 128.58 (d, aromatic), 128.75 (di aromatic), 130.60 (d, aromatic), 131.43 (d, aromatic), 131.56 (aromatic), 137.02 (s, aromatic), 137.40 (d, aromatic), 138.28 (s, aromatic), 142.58 (s, aromatic), 158.09 (s, aromatic), 165.12 (s, CO). HRMS calcd. for C17H13IN2O: 388.0073. Found: 388.0077.

Workup

  1. stirringAfter stirring for 1 h
  2. stirringThe mixture was stirred under Ar for 7 h
  3. customquenched
  4. additionby adding H2O (8 mL)
  5. extractionThe resulting mixture was extracted with CH2Cl2 (3×20 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was purified on column chromatography (SiO2, 35% ethyl acetate in hexane, 0.1% Et3N)

Sources & evidence

ORD record
ord-fb59e81d2e08498ea8c70ab96f6c7980
Source dataset
uspto-grants-1999_12
Patent number
US05998624

Reaction notes

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