Triphenylphosphine → HCID 71086428, compound

HRID 1524190Notes

Reaction equation

HRID 1524190 reaction equation
[N:1]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][C@H:14]([CH2:18][OH:19])[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[N:25][CH:26]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:20][C:21]1[CH:22]=[C:23]([O:19][CH2:18][C@H:14]2[O:15][CH2:16][CH2:17][N:12]([CH2:11][CH2:10][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)[CH2:13]2)[CH:24]=[N:25][CH:26]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5823053-Hydroxy-5-chloropyridineHCID 5363146Diisopropyl azodicarboxylateHCID 71062870HCID 71062870, compound

Product 1

HCID 71086428HCID 71086428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 27s was synthesised by essentially the same procedure as compound 18s (Example 16). Compound 51 (Example 10; 80 mg, 0.30 mmol), was reacted with 5-chloro-3-hydroxypyridine (59 mg, 0.46 mmol), PPh3 (120 mg, 0.46 mmol), DIAD (90 μl, 0.46 mmol) and THF (1.5 ml). The reaction mixture was stirred at RT for 48 hrs. After this time, the solvent was removed and the crude mixture purified twice by flash column chromatography (silica, DCM/MeOH 1:0 to 94:6, then Hex/EtOAc 1:0 to 0:1) to afford compound 27s (71 mg, 91%). Analyses were performed on the free base. The compound was re-purified (36.7 mg, purity 100%), and converted to the HCl salt for assaying.

Workup

  1. customAfter this time, the solvent was removed
  2. customthe crude mixture purified twice by flash column chromatography (silica, DCM/MeOH 1:0 to 94:6

Sources & evidence

ORD record
ord-6ae2b6315622480488aa962b8af15ece
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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