Water → HCID 86586313, compound

HRID 396349Notes

Reaction equation

HRID 396349 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][C@H:20]([CH2:22]OS(C)(=O)=O)[O:19][C:18]2=[O:28])=[CH:13][C:12]=1[F:29].[N-:30]=[N+:31]=[N-:32].[Na+].O>CN(C=O)C>[N:30]([CH2:22][C@@H:20]1[O:19][C:18](=[O:28])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([N:3]3[CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])=[C:12]([F:29])[CH:13]=2)[CH2:21]1)=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86586314HCID 86586314, compound

Product 1

HCID 86586313HCID 86586313, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To the mesylate from Example 2 (0.95 g, 1.78 mmols) in DMF (25 mL) was added sodium azide (0.47 g, 7.23 mmols) and heated to 70° C. for 16 hrs. After cooling to rt water was added and the mixture extracted with ethyl acetate (6×25 mL), washed with brine (4×10 mL), dried over Na2SO4, concentrated to give 0.48 g of a tan solid. MS (M+1)=354 m/z.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate (6×25 mL)
  3. washwashed with brine (4×10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e57f1d41ca0484d828487c0a40fc83d
Source dataset
uspto-grants-2003_08
Patent number
US06608081B2

Reaction notes

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