Ammonia → HCID 178505137, compound

HRID 639433Notes

Reaction equation

HRID 639433 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[NH:11][C:12]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)=[N+]=[N-].N([C@H]1CC[C@H](C(O)=O)CC1)=[N+]=[N-].C1(C2C=CC(N)=C(N)C=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:70][S:71](Cl)(=[O:73])=[O:72].N>C(N(CC)CC)C.O.C1COCC1>[CH3:70][S:71]([NH:1][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[NH:11][C:12]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)(=[O:73])=[O:72]

Participants

10

Reactant 6

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 31297Methanesulfonyl chlorideHCID 6452000(1,1'-Biphenyl)-3,4-diamineHCID 178514617HCID 178514617, compoundHCID 178514618HCID 178514618, compound

Product 1

HCID 178505137HCID 178505137, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution in a solvent mixture of THF (4.0 mL) and water (1.0 mL) of 2-(trans-4-azidocyclohexyl)-5-phenylbenzimidazole (73.1 mg) as prepared by reacting trans-4-azidocyclohexanecarboxylic acid with 4-phenyl-1,2-phenylenediamine under the same conditions as described in Example 1-3) was added triphenylphosphine (72.0 mg), followed by stirring at room temperature for 1 hr. A portion of the reaction solution was admixed with methanesulfonyl chloride and triethylamine, followed by stirring at the same temperature for 1 hr., and the resultant reaction solution was admixed with conc. aqueous ammonia, followed by concentration under reduced pressure. The residue was separated and purified on a collective thin-layer chromatograph (chloroform:methanol=15:1) to give the title compound.

Workup

  1. customas prepared
  2. stirringby stirring at the same temperature for 1 hr
  3. custom, and the resultant reaction solution
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was separated
  6. custompurified on a collective thin-layer chromatograph (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-4bf29c1f7ff5444f98ba196f378fa309
Source dataset
uspto-grants-2010_04
Patent number
US07691860B2

Reaction notes

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