Sodium Azide → HCID 86590429, compound

HRID 1986967Notes

Reaction equation

HRID 1986967 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]4[CH2:20][C@H:19]4[CH2:21]OS(C)(=O)=O)[CH2:13][CH2:12]3)=[CH:9][S:8][C:7]=2[CH:27]=1.[N-:30]=[N+:31]=[N-:32].[Na+]>CC#N>[N:30]([CH2:21][C@@H:19]1[CH2:20][C@H:18]1[CH2:17][N:14]1[CH2:13][CH2:12][N:11]([C:10]2[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:28])([F:29])[F:1])=[CH:27][C:7]=3[S:8][CH:9]=2)[CH2:16][CH2:15]1)=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium Azide2×HCID 86590430HCID 86590430, compound

Product 1

HCID 86590429HCID 86590429, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
47 °C

Procedure

A mixture of Methanesulfonic acid (1R, 2R )-2-[4-(6-trifluoromethyl-benzo[b]thiophen-3-yl )-piperazin-1-ylmethyl]-cyclopropylmethyl ester (3.995 g, 8.92 mmol), NaN3 (1.16 g, 17.85 mmol ) and anhydrous CH3CN (60 mL ) was stirred at 47° C. under N2 for 4 h, then an additional quantity of NaN3 (580 mg, 8.92 mmol ) was added. Stirring was continued at 47° C. for a further 4 h. After cooling to rt, the mixture was filtered through Celite 545, washed with CH3CN. The combined filtrate and washings were concentrated and then separated by Prep LC (heptane/EtOAc—70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 100% EtOAc) to give the desired product (1.5 g, 43%).

Workup

  1. stirringStirring
  2. waitwas continued at 47° C. for a further 4 h
  3. temperatureAfter cooling to rt
  4. filtrationthe mixture was filtered through Celite 545
  5. washwashed with CH3CN
  6. concentrationThe combined filtrate and washings were concentrated
  7. customseparated by Prep LC (heptane/EtOAc—70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 100% EtOAc)

Sources & evidence

ORD record
ord-2cf84a4b542c4ef7a2471634a2fe6c66
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

Loading…