Methanesulfonyl chloride → HCID 86671465, compound

HRID 1530538Notes

Reaction equation

HRID 1530538 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([CH:23]([OH:25])[CH3:24])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:25][CH:23]([C:14]1[CH:13]=[C:12]2[C:17]([O:18][CH2:19][CH2:20][N:21]3[C:11]2=[N:10][C:9]([C:8]2[N:4]([CH:2]([CH3:1])[CH3:3])[N:5]=[CH:6][N:7]=2)=[CH:22]3)=[CH:16][CH:15]=1)[CH3:24])(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68312910HCID 68312910, compound

Product 1

HCID 86671465HCID 86671465, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethan-1-ol (200 mg, 0.590 mmol) in DCM (20 mL) at 0° C. was added TEA (296 mg, 2.93 mmol) and MsCl (136 mg, 1.19 mmol). The reaction mixture was stirred 0° C. for 2 h and then allowed to warm to room temperature. The reaction was quenched with sat. NaHCO3 (10 mL), the resultant mixture was washed with sat. NaCl (20 mL). The organic phase was dried and concentrated to afford 1-{4-[1-(Propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethyl methanesulfonate (246 mg, 100% yield) as a brown solid, which was directly used in next step without further purification.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with sat. NaHCO3 (10 mL)
  3. washthe resultant mixture was washed with sat. NaCl (20 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-593f412eb0be432e853a75a9b750f1e1
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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