Triphenylphosphine → HCID 67103293, compound

HRID 2079608Notes

Reaction equation

HRID 2079608 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.[OH:36][CH:37]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]1.O[C:45]1[CH:46]=[CH:47][CH:48]=[C:49]2[C:54]=1[N:53]=[C:52]([NH:55][C:56]1[CH:57]=[C:58]([S:62]([NH2:65])(=[O:64])=[O:63])[CH:59]=[CH:60][CH:61]=1)[N:51]=[CH:50]2>C1COCC1>[CH3:43][N:40]1[CH2:41][CH2:42][CH:37]([O:36][C:45]2[CH:46]=[CH:47][CH:48]=[C:49]3[C:54]=2[N:53]=[C:52]([NH:55][C:56]2[CH:57]=[C:58]([S:62]([NH2:65])(=[O:64])=[O:63])[CH:59]=[CH:60][CH:61]=2)[N:51]=[CH:50]3)[CH2:38][CH2:39]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 67101622HCID 67101622, compound

Product 1

HCID 67103293HCID 67103293, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0.3M solution of triphenylphosphine (1.5 eq) in THF was added di-tert-butylazodicarboxylate (1.5 eq). The mixture was stirred 15 minutes at ambient temperature. 4-Hydroxy-1-methylpiperidine (4.5 eq) was added. The mixture was stirred 15 minutes at ambient temperature. 3-(8-Hydroxyquinazolin-2-ylamino)benzenesulfonamide (1.0 eq) was added. The mixture was stirred an additional 1 hour. The crude mixture was concentrated, purified by RPHPLC, and lyophilized to give the desired product in 24.2% yield ES/MS m/z 414 (MH+).

Workup

  1. stirringThe mixture was stirred 15 minutes at ambient temperature
  2. stirringThe mixture was stirred an additional 1 hour
  3. concentrationThe crude mixture was concentrated
  4. custompurified by RPHPLC

Sources & evidence

ORD record
ord-528038f3722c451bb27c15f851e236ee
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

Loading…