Methanesulfonyl chloride → HCID 24801301, compound

HRID 469809Notes

Reaction equation

HRID 469809 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[O:16][C:15]([NH:18][C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)=[N:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[CH3:26][O:25][C:23]1[CH:24]=[C:19]([NH:18][C:15]2[O:16][C:17]3[C:9]([C:6]4[CH:7]=[CH:8][C:3]([CH2:2][NH:1][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:4][CH:5]=4)=[CH:10][CH:11]=[CH:12][C:13]=3[N:14]=2)[CH:20]=[C:21]([O:29][CH3:30])[C:22]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 24801299HCID 24801299, compound

Product 1

HCID 24801301HCID 24801301, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.10 g (0.247 mmol) [7-(4-aminomethyl-phenyl)-benzooxazol-2-yl]-(3,4,5-trimethoxy-phenyl)-amine (example 29) and 0.037 g (0.32 mmol) methanesulfonyl chloride in 4 ml pyridine is stirred for 1.5 h at room temperature. Then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with 0.1N NaOH solution and water, dried over MgSO4, filtered and the filtrate is concentrated in vacuo and co-evaporated twice with toluene. The residue is purified by crystallisation from dichloromethane to afford the title compound as off-white crystals. Rt=2.20 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min); MS: 474 (M+1)+.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted 3× with EtOAc
  3. washThe combined organic layers are washed with 0.1N NaOH solution and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by crystallisation from dichloromethane

Sources & evidence

ORD record
ord-a0fdb7748a4c438280fc514f3be66ee6
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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