Triphenylphosphine → HCID 178454107, compound

HRID 707291Notes

Reaction equation

HRID 707291 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].[Br:14][C:15]1[N:20]=[C:19]2[N:21]([CH:25]3[CH2:27][CH2:26]3)[C:22](=[O:24])[NH:23][C:18]2=[N:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([N:23]2[C:18]3=[N:17][CH:16]=[C:15]([Br:14])[N:20]=[C:19]3[N:21]([CH:25]3[CH2:26][CH2:27]3)[C:22]2=[O:24])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86694158HCID 86694158, compoundHCID 178454126HCID 178454126, compound

Product 1

HCID 178454107HCID 178454107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of tert-butyl(trans-3-hydroxycyclobutyl)carbamate (0.250 g, 1.335 mmol), 6-bromo-1-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.334 g, 1.309 mmol) and triphenylphosphine (0.520 g, 1.983 mmol) in THF (10 ml) was added DIAD (0.400 ml, 2.032 mmol) dropwise via syringe. After 10 min the reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in MeOH/EtOAc, evaporated onto silica gel and purified by flash chromatography (Isco (25 gram)) eluting with EtOAc:hexanes (0:1-1:1) to give a light-yellow solid. ESI MS 445.9, 447.8 [M+Na].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in MeOH/EtOAc
  3. customevaporated onto silica gel
  4. custompurified by flash chromatography (Isco (25 gram))
  5. washeluting with EtOAc:hexanes (0:1-1:1)
  6. customto give a light-yellow solid

Sources & evidence

ORD record
ord-49e03840244c436e8fd6f5eedd8fc8bb
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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