Triphenylphosphine → HCID 66558838, compound

HRID 1530568Notes

Reaction equation

HRID 1530568 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:24])=[N:5]1)([CH3:3])[CH3:2].[F:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[CH:32](O)[CH3:33].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[F:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[CH:32]([O:23][C:21]1[CH:20]=[CH:19][C:16]2[C:17]3[N:11]([CH:10]=[C:9]([C:8]4[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[C:6]([CH3:24])[N:7]=4)[N:18]=3)[CH2:12][CH2:13][O:14][C:15]=2[CH:22]=1)[CH3:33]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13129579HCID 13129579, compoundHCID 136414067HCID 136414067, compound

Product 1

HCID 66558838HCID 66558838, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol (300 mg, 0.92 mmol), 1-(3-fluoropyridin-4-yl)ethanol (195 mg, 1.38 mmol) and PPh3 (411 mg, 1.57 mmol) in dioxane (5 mL) was added DIAD (325 μL, 1.57 mmol) and the resulting yellow solution stirred at RT for 2 h. The reaction mixture was partitioned between EtOAc and 1M NaOH, the organic phase dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc) then triturated with TBME affording 167 (220 mg, 53%). LCMS: RT 4.36 min [M+H]+ 449.3. 1H NMR (DMSO, 400 MHz): δ 8.47 (1H, d, J=1.61 Hz), 8.39-8.36 (2H, m), 7.56 (1H, s), 7.39-7.34 (1H, m), 6.69 (1H, dd, J=8.99, 2.60 Hz), 6.46 (1H, d, J=2.57 Hz), 5.91-5.83 (1H, m), 5.66 (1H, q, J=6.47 Hz), 4.44-4.43 (2H, m), 4.39-4.35 (2H, m), 2.40 (3H, s), 1.68 (3H, d, J=6.45 Hz), 1.55 (6H, d, J=6.65 Hz)

Workup

  1. customThe reaction mixture was partitioned between EtOAc and 1M NaOH
  2. dry with materialthe organic phase dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc)
  5. customthen triturated with TBME affording 167 (220 mg, 53%)

Sources & evidence

ORD record
ord-bb577e20f9fa4cbea9b59fe32bc8c86f
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…