1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22725084, compound

HRID 2086586Notes

Reaction equation

HRID 2086586 reaction equation
C1(P([N:15]=[N+:16]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=1[Cl:73])[N:37]1[CH:42]2[CH2:43][CH2:44][CH:38]1[CH2:39][C:40]([C:46]1[N:51]=[C:50]([CH2:52][NH:53]C(NCCNC(=O)OC(C)(C)C)=O)[CH:49]=[CH:48][CH:47]=1)([OH:45])[CH2:41]2>>[N:53]([CH2:52][C:50]1[N:51]=[C:46]([C:40]2([OH:45])[CH2:39][CH:38]3[N:37]([CH:36]([C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=4[Cl:73])[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[Cl:29])[CH:42]([CH2:43][CH2:44]3)[CH2:41]2)[CH:47]=[CH:48][CH:49]=1)=[N+:15]=[N-:16]

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 20722945HCID 20722945, compound

Product 1

HCID 22725084HCID 22725084, compound

Procedure

Add diphenylphosphoryl azide (272 mg, 0.99 mmol) and 1,8-diazabicyclo-[5,4,0]undec-7-ene (150 mg, 0.99 mmol) to the product from Step 4 (404 mg, 0.86 mmol) at 0° C., stir for 20 min., warm to RT then stir at 50° C. for 1 h. Cool to RT and stir overnight. Quench the reaction with H2O and saturated aqueous NH4Cl , extract with CH2Cl2, dry and concentrate. Purify the residue by column chromatography to give the desired compound.

Workup

  1. stirringthen stir at 50° C. for 1 h
  2. temperatureCool to RT
  3. stirringstir overnight
  4. customQuench
  5. customthe reaction with H2O and saturated aqueous NH4Cl
  6. extractionextract with CH2Cl2
  7. customdry
  8. concentrationconcentrate
  9. customPurify the residue by column chromatography

Sources & evidence

ORD record
ord-e8992e6f3b224bfeb9ad830c481b8107
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

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