Triphenylphosphine → HCID 178454106, compound

HRID 707277Notes

Reaction equation

HRID 707277 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@@H:10](O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:33]1([N:36]2[C:44]3[C:39](=[N:40][CH:41]=[CH:42][CH:43]=3)[NH:38][C:37]2=[O:45])[CH2:35][CH2:34]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([N:38]2[C:39]3=[N:40][CH:41]=[CH:42][CH:43]=[C:44]3[N:36]([CH:33]3[CH2:34][CH2:35]3)[C:37]2=[O:45])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 183348751-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-oneHCID 178454125HCID 178454125, compound2×

Product 1

HCID 178454106HCID 178454106, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl(cis-3-hydroxycyclobutyl)carbamate (Intermediate 71) (0.502 g, 2.68 mmol), triphenylphosphine (Sigma-Aldrich, 0.932 ml, 4.02 mmol), 1-cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.47 g, 2.68 mmol) in THF (10.73 ml) cooled to 0° C. was added diisopropyl azodicarboxylate (Sigma-Aldrich, 0.791 ml, 4.02 mmol) dropwise. The ice bath was removed after 1 h of stirring to allow the mixture to warm to room temperature. After an additional 3 h stirring, the reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 solution. The organic layer was directly loaded onto a Biotage samplet. Purification (0-100% EtOAc/hexane) produced the title compound that solidified upon drying, which was advanced to next step directly without further purification. M+1: 345.0.

Workup

  1. customThe ice bath was removed after 1 h
  2. stirringAfter an additional 3 h stirring
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with saturated NaHCO3 solution
  5. customPurification (0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-790017886ffb45108575169cdc3c9257
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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