Methyl iodide → HCID 21886161, compound

HRID 2216067Notes

Reaction equation

HRID 2216067 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C:9]1([C:15]2[CH:16]=[C:17]([S:21]([C:24]3[CH:25]=[C:26]([C:31]([NH2:33])=[NH:32])[S:27][C:28]=3[S:29][CH3:30])(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[H-].[Na+].IC>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:2][O:8][C:9]1([C:15]2[CH:16]=[C:17]([S:21]([C:24]3[CH:25]=[C:26]([C:31]([NH2:33])=[NH:32])[S:27][C:28]=3[S:29][CH3:30])(=[O:22])=[O:23])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86590789HCID 86590789, compound

Product 1

HCID 21886161HCID 21886161, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the BOC-protected amidine (46 mg, 0.09 mmol) (prepared in example 149) in 0.2 mL of DMF at 25° C. was added NaH (60% oil dispersion, 5.7 mg, 0.14 mmol). The reaction was allowed to stir for 20 mins then iodomethane (6 uL, 0.09 mmol) was added and the reaction stirred for additional 12 hrs. The solvent was evaporated and the crude material purified by flash chromatography to give the title compound as a BOC protected amidine, which was deprotected in 2 mL of 50% TFA/DCM (25° C., 1 hr) to give the title compound (11.5 mg, 20%) as a yellow solid: 1H NMR (400 MHz, CD3OD) δ 8.34 (s, 1H), 8.14 (m, 1H), 7.92 (m, 1H), 7.80 (m, 1H), 7.66 (m, 1H), 3.89 (m, 4H), 3.00 (s, 3H), 2.74 (s, 3H), 2.02 (m, 4H). Mass spectrum (ESI, m/z) calcd. for C18H22N2O4S3 426.1, found 427.1 (M+H).

Workup

  1. stirringthe reaction stirred for additional 12 hrs
  2. customThe solvent was evaporated
  3. customthe crude material purified by flash chromatography

Sources & evidence

ORD record
ord-875a6c85fbfa46e29180b1de92cf2cb4
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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