Tetrahydrofuran → Diisopropyl diazene-1,2-dicarboxylate

HRID 540803Notes

Reaction equation

HRID 540803 reaction equation
N1C2C3C=CC=CC=3N=CC=2[N:3]=[C:2]1[OH:14].C1(P([C:28]2[CH:33]=[CH:32]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.OC1CC[N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])C)=[O:42])CC1.C1C[O:51]CC1>>[N:3]([C:2]([O:14][CH:33]([CH3:32])[CH3:28])=[O:51])=[N:38][C:41]([O:43][CH:44]([CH3:46])[CH3:47])=[O:42]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178517343HCID 178517343, compound2×

Product 1

HCID 75555Diisopropyl diazene-1,2-dicarboxylate

Procedure

Alternatively, a compound of Formula XXXV can react with a 1H-imidazo[4,5-c]quinolinol of Formula XXIII under the Mitsunobu reaction conditions described in step (9) of Reaction Scheme I. For example, combining a 1H-imidazo[4,5-c]quinolinol of Formula XXIII, triphenylphosphine, and tert-butyl 4-hydroxy-1-piperdinecarboxylate in THF at 5° C. or ambient temperature and slowly adding diisopropyl azodicarboxylate provides a compound of Formula XXXVII wherein Za is a bond and R10 is pentylene.

Workup

  1. customdescribed in step (9) of Reaction Scheme I
  2. customat 5° C.

Sources & evidence

ORD record
ord-37e7fc0df7bf4e38b2370288a90d2956
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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