Sodium Azide → HCID 86725101, compound

HRID 634157Notes

Reaction equation

HRID 634157 reaction equation
CS([C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:14]=[C:13]3[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:27]=2)=[N:7][N:6]=1)(=O)=O.[N-:38]=[N+:39]=[N-:40].[Na+]>CS(C)=O.O>[N:38]([C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH:14]=[C:13]3[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)[N:27]=2)=[N:7][N:6]=1)=[N+:39]=[N-:40]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 68328178HCID 68328178, compound

Product 1

HCID 86725101HCID 86725101, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate (300 mg, 0.554 mmol) in DMSO (3 mL) was added sodium azide (215.8 mg, 3.32 mmol). The reaction was heated at 55-65° C. for 4 h, then diluted with H2O and extracted with EtOAc (80 mL×3). The combined organic layers were washed with water (50 mL×4), dried, filtered and concentrated to give the crude material (240 mg). MS (ESI, pos. ion) m/z: 505 (M+1).

Workup

  1. extractionextracted with EtOAc (80 mL×3)
  2. washThe combined organic layers were washed with water (50 mL×4)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f131bf4448a4d0bbb94d8586bbacb60
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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