Sodium Azide → HCID 118676845, compound

HRID 630471Notes

Reaction equation

HRID 630471 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[C@H:16]2[CH2:20][CH2:19][N:18]([C:21]([C:23]3[CH:31]=[C:30]4[C:26]([C:27]([S:45]([CH3:47])=[O:46])=[CH:28][N:29]4[C:32]4[N:37]=[CH:36][C:35]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=5[F:44])=[CH:34][N:33]=4)=[CH:25][CH:24]=3)=[O:22])[CH2:17]2)(=O)=O)=CC=1>CN(C=O)C>[N:1]([C@@H:20]1[CH2:16][CH2:17][N:18]([C:21]([C:23]2[CH:31]=[C:30]3[C:26]([C:27]([S:45]([CH3:47])=[O:46])=[CH:28][N:29]3[C:32]3[N:37]=[CH:36][C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[F:44])=[CH:34][N:33]=3)=[CH:25][CH:24]=2)=[O:22])[CH2:19]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 118676857HCID 118676857, compound

Product 1

HCID 118676845HCID 118676845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (0.31 g, 4.79 mmol) was added to a solution of 68a) (0.75 g, 1.37 mmol) in DMF (8.65 mL) and the resulting mixture was stirred at 60° C. for 2 h. After cooling to ambient temperature, the reaction mixture was poured onto water and extracted with dichloromethane (3×30 mL). The organic phase was dried over sodium sulfate and concentrated. The remnant was purified by flash column chromatography [silica; 2.5% methanol in dichloromethane]. White solid. Yield: 0.4 g (59% of theory). HPLC-MS (method 4): Rt=3.04 min; m/z [M+H]+=490.2

Workup

  1. temperatureAfter cooling to ambient temperature
  2. additionthe reaction mixture was poured onto water
  3. extractionextracted with dichloromethane (3×30 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe remnant was purified by flash column chromatography [silica; 2.5% methanol in dichloromethane]

Sources & evidence

ORD record
ord-7bfa09defc414c1da2431bd0ce59ba34
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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