Nitrogen → HCID 86730387, compound

HRID 531219Notes

Reaction equation

HRID 531219 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:26])[NH:6]2.N#N.[H-].[Na+].Cl[C:32]([O:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:33]>C1COCC1>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:24][CH3:25])[N:15]=[CH:14][N:13]=[C:12]2[O:11][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[N:6]([C:32]([O:34][C:35]1[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=1)=[O:33])[C:5]([CH3:26])=[CH:4]2

Participants

6

Reactant 4

HCID 947Nitrogen2×HCID 24758Sodium hydrideHCID 821294-Nitrophenyl chloroformateHCID 86730388HCID 86730388, compound

Product 1

HCID 86730387HCID 86730387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Compound 11 (300 mg, 0.85 mmol) in dry THF was sparged with N2, then NaH (68 mg of 60% dispersion, 1.7 mmol) was added in a single portion. While still sparging with N2, 4-nitrophenyl chloroformate (341 mg, 1.7 mmol) was added and the reaction stirred at room temperature for 1 hour. Solvent was evaporated by rotary evaporator and the product precipitated from ethyl acetate/diethyl ether and filtered. The crude solid was washed with methanol (20 mL) to yield Compound 12 as crude yellow solid, which was taken directly to the next reaction.

Workup

  1. additionwas added
  2. customSolvent was evaporated by rotary evaporator
  3. customthe product precipitated from ethyl acetate/diethyl ether
  4. filtrationfiltered
  5. washThe crude solid was washed with methanol (20 mL)

Sources & evidence

ORD record
ord-8191910139c3444483a4b5d4413940d1
Source dataset
uspto-grants-2016_05
Patent number
US09353123B2

Reaction notes

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