Triethylamine → HCID 19601669, compound

HRID 610654Notes

Reaction equation

HRID 610654 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]([N:20]([CH3:25])[CH2:21][CH2:22][CH2:23]O)=[O:19])[N:9]=1.CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[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]([N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][S:34]([CH3:33])(=[O:36])=[O:35])=[O:19])[N:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19601674HCID 19601674, compound

Product 1

HCID 19601669HCID 19601669, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-iodophenyl)-N-methyl-N-(3-hydroxypropyl)-3-isoquinolinecarbo-xamide (20 mg, 0.045 mmol), DMAP (5.5 mg, 0.045 mmol), and Et3N (0.02 mL, 0.14 mmol) in CH2Cl2 (2 mL) at 0° C. was added dropwise MsCl (0.006 mL, 0.77 mmol). The resulting mixture was stirred at 0° C. and monitored by TLC. After stirring at 0° C. for 4 h, TLC showed that no starting material left. Then, it was transferred into separatory funnel and washed with H2O (15 mL) The organic layer was dried (MgSO4), and filtered. The filtrate was concentrated in vacuo. The residue was purified on column (silica gel, 2% MeOH/CH2Cl2, 0.1% Et3N), thereby affording an oil (16 mg, 68%). 1H NMR (CDCl3) d 2.12-2.22 (m, 2 H, CH2), 2.77, 3.06 (two s, total 3 H, --SO2Me), 3.17, 3.20 (two s, total 3 H, N--Me), 3.62-3.82 (m, 2 H, N--CH2), 4.15 (t, J=6.0 Hz, 1 H, CH2O), 4.39 (t, J=6.0 Hz, 1 H, CH2O), 7.19-7.27 (m, 1 H, aromatic), 7.39-7.41 (m, 1 H, aromatic), 7.48-7.64 (m, 3 H, aromatic), 7.73-7.79 (m, 1 H, aromatic), 7.96-8.05 (m, 2 H, aromatic), 8.12, 8.24 (two s, total 1 H, aromatic). HRFABMS Cacld. for C21H21ILiN2O4S: 531.0427 (M+Li)+. Found: 531.0443.

Workup

  1. stirringAfter stirring at 0° C. for 4 h
  2. waitleft
  3. customThen, it was transferred into separatory funnel
  4. washwashed with H2O (15 mL) The organic layer
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe residue was purified on column (silica gel, 2% MeOH/CH2Cl2, 0.1% Et3N)

Sources & evidence

ORD record
ord-53413bbf294740b089d0b6db63d4c3f7
Source dataset
uspto-grants-1999_12
Patent number
US05998624

Reaction notes

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