Ammonia → HCID 69516679, compound

HRID 855526Notes

Reaction equation

HRID 855526 reaction equation
C[N:2](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[O:23]=[S:24]1(=[O:49])[C:29]2[CH:30]=[C:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][C:43](O)=[O:44])=[CH:37][CH:36]=3)[CH:32]=[CH:33][C:28]=2[N:27]2[CH2:46][CH2:47][CH2:48][C:26]2=[N:25]1.C(N(C(C)C)CC)(C)C.N.Cl>C(Cl)Cl.CCOC(C)=O>[O:23]=[S:24]1(=[O:49])[C:29]2[CH:30]=[C:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][C:43]([NH2:2])=[O:44])=[CH:37][CH:36]=3)[CH:32]=[CH:33][C:28]=2[N:27]2[CH2:46][CH2:47][CH2:48][C:26]2=[N:25]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69517150HCID 69517150, compound

Product 1

HCID 69516679HCID 69516679, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

415 mg (1.30 mmol) of TBTU are added to a suspension (500 mg, 1.30 mmol) of the compound obtained in Step B of Example 2 in 25 ml of CH2Cl2. The suspension is stirred at ambient temperature for 10 minutes and 293 μl (1.68 mmol) of diisopropylethylamine are added. The reaction mixture becomes a solution and stirring is continued for 10 minutes. The solution is then saturated with ammonia gas and stirring is continued for 30 minutes. Thin-layer chromatography (AcOEt) indicates that all the starting material has disappeared. The reaction mixture is then acidified by adding 1N HCl; the organic phase is decanted off, washed (water and then saturated NaCl solution), dried (MgSO4) and evaporated. The residue is triturated in Et2O and the white solid formed is filtered off to yield the title product.

Workup

  1. stirringstirring
  2. waitis continued for 10 minutes
  3. waitis continued for 30 minutes
  4. customthe organic phase is decanted off
  5. washwashed (water
  6. dry with materialsaturated NaCl solution), dried (MgSO4)
  7. customevaporated
  8. customThe residue is triturated in Et2O
  9. customthe white solid formed
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-bb66197ae61a4ddba4bb152871d51570
Source dataset
uspto-grants-2007_08
Patent number
US07262190B2

Reaction notes

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