Triethylamine → HCID 86666459, compound

HRID 872280Notes

Reaction equation

HRID 872280 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[C:21]([CH2:22][OH:23])=[CH:20][CH:19]=[CH:18][N:17]=1.CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:23][CH2:22][C:21]1[C:16]([O:15][C:3]2[CH:4]=[CH:5][C:6]3[N:7]([CH2:11][CH:12]4[CH2:13][CH2:14]4)[N:8]=[N:9][C:10]=3[C:2]=2[Br:1])=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67954969HCID 67954969, compound

Product 1

HCID 86666459HCID 86666459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2-{[4-bromo-1-(cyclopropylmethyl)-1H-1,2,3-benzotriazol-5-yl]oxy}pyridin-3-yl)methanol (195) (1 g, 2.62 mmol, 1.0 equiv.) and Et3N (1.1 ml, 7.85 mmol, 3.0 equiv.) in DCM (13 ml) were cooled to 0° C., followed by MsCl (265 ul, 3.40 mmol, 1.3 equiv.), then stirred @ 0° C. for 1 hour. The reaction mixture then quenched with NaHCO3(sat) and extracted with DCM (2×40 ml). The combined DCM layer was washed with brine and dried over Na2SO4, filtered and concentrated down solvent. LRMS m/z (M+H) 486.8 and 488.8 found, 487.0 and 489.0 required.

Workup

  1. customThe reaction mixture then quenched with NaHCO3(sat)
  2. extractionextracted with DCM (2×40 ml)
  3. washThe combined DCM layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated down solvent

Sources & evidence

ORD record
ord-031e25ffa0744bc687101c9c2215cd5a
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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