Methanesulfonyl chloride → HCID 57786154, compound

HRID 1628664Notes

Reaction equation

HRID 1628664 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]1[C:9]2[N:10]([CH2:24][CH2:25][CH2:26]O)[C:11]([NH:13][C:14]3[C:15]([O:22][CH3:23])=[N:16][C:17]([O:20][CH3:21])=[N:18][CH:19]=3)=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2].CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:21][O:20][C:17]1[N:16]=[C:15]([O:22][CH3:23])[C:14]([N:13]2[C:11]3=[N:12][C:8]4[C:9](=[C:4]([N:3]([CH2:1][CH3:2])[CH2:28][CH3:29])[CH:5]=[CH:6][CH:7]=4)[N:10]3[CH2:24][CH2:25][CH2:26]2)=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68762386HCID 68762386, compound

Product 1

HCID 57786154HCID 57786154, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-{7-(diethylamino)-2-[(2,4-dimethoxypyrimidin-5-yl)amino]-1H-benzimidazol-1-yl}propan-1-ol (Reference Example 97; 90 mg, 0.224 mmol) in pyridine (2.0 mL) was added methanesulfonyl chloride (0.035 mL, 0.449 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 hr. Aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a solid, which was recrystallized from n-hexane/ethyl acetate to give the title compound (50 mg, 0.131 mmol, 58%) as a pale brown solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a solid, which
  6. customwas recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-9cd71d522e054ba7b1293685fd9e9e56
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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