Triethylamine → HCID 15870542, compound

HRID 610646Notes

Reaction equation

HRID 610646 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([OH:20])=O)[N:9]=1.Cl.CN.C[CH2:25][N:26](CC)CC>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([NH:26][CH3:25])=[O:20])[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 19601667HCID 19601667, compound

Product 1

HCID 15870542HCID 15870542, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(2-iodophenyl)-3-isoquinolinecarboxylic acid (0.1868 g, 0.5 mmol), benzotriazol-1-yloxy-tris (demethylamino) phosphonium hexafluorophosphate (BOP) (0.2219 g, 0.5 mmol), Methylamine hydrochloride (0.1019 g, 1.5 mmol) in DMF (8 mL) was added Et3N (0.42 mL, 4.5 mmol). The resulting mixture was stirred under Ar at room temperature for 7 h and quenched by adding H2O (10 mL). The mixture was extracted with CH2Cl2 (3×15 mL). The combined organic layers were dried (MgSO4), filtered. The filtrate was concentrated in vacuo. The residue was purified on column (SiO2, 50% ethyl acetate/hexane, 0.1% Et3N), thereby giving a white foam (0.1237 g, 65%). mp: 167-168° C. 1H NMR (CDCl3) d 3.03, 3.05 (two s, 3 H, N-methyl), 7.25 (t, J=10.5 Hz, 1 H, aromatic), 7.39 (d, J=7.5 Hz, 1 H), 7.48-7.68 (m, 3 H, aromatic), 7.75 (t, J=9 Hz, 1 H, aromatic), 8.02-8.06 (m, 2 H, aromatic), 8.18 (br s, 1 H, NH), 8.65 (s, aromatic). 13C NMR (CDCl3) d 26.13 (q, N-methyl), 97.79 (s, C--I), 120.02 (d, aromatic), 127.29 (d, aromatic), 127.75 (d, aromatic), 127.98 (d, aromatic), 128.53 (d, aromatic), 128.76 (d, aromatic), 130 13 (d, aromatic), 130.31 (d, aromatic), 130.81 (d, aromatic), 136.81 (s, aromatic), 139.42 (d, aromatic), 142.59 (s, aromatic), 143.30 (s, aromatic), 160.79 (s, aromatic), 165.32 (s, --CO--). HRMS calcd. for C17H13IN3IN2O: 388.0073. Found: 388.0070.

Workup

  1. customquenched
  2. additionby adding H2O (10 mL)
  3. extractionThe mixture was extracted with CH2Cl2 (3×15 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified on column (SiO2, 50% ethyl acetate/hexane, 0.1% Et3N)

Sources & evidence

ORD record
ord-8097cef0790d4938960033f4f061434f
Source dataset
uspto-grants-1999_12
Patent number
US05998624

Reaction notes

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