Water → HCID 178433884, compound

HRID 59045Notes

Reaction equation

HRID 59045 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([N:26]2[N:49]=[C:48]([CH3:50])/[C:29](=[N:30]/[NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[C:36]([C:39]4[CH:40]=[CH:41][CH:42]=[C:43](C(O)=O)[CH:44]=4)[C:37]=3[OH:38])/[C:27]2=[O:28])=[CH:23][C:24]=1[CH3:25].CC[N:53]([CH2:56]C)CC.[OH2:58]>C(Cl)Cl>[CH3:25][C:24]1[CH:23]=[C:22]([N:26]2[C:27](=[O:28])/[C:29](=[N:30]\[NH:31][C:32]3[C:37]([OH:38])=[C:36]([C:39]4[CH:40]=[CH:41][CH:42]=[C:43]([N:15]5[C:56](=[O:58])[NH:53][N:17]=[N:16]5)[CH:44]=4)[CH:35]=[CH:34][CH:33]=3)/[C:48]([CH3:50])=[N:49]2)[CH:21]=[CH:20][C:19]=1[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azide2×HCID 178433880HCID 178433880, compound

Product 1

HCID 178433884HCID 178433884, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Diphenyl phosphoryl azide (196 μL, 0.9 mmol) was added to a stirred solution of Eltrombopag (365 mg, 0.83 mmol) and Et3N (140 μL, 1.0 mmol) in CH2Cl2 (10 mL) at 0° C. under an atmosphere of nitrogen. The mixture was stirred at 0° C. for 2 min, then allowed to warm to room temperature and stirred for 2 hr. Further aliquots of diphenyl phosphoryl azide (196 μL, 0.9 mmol) and Et3N (140 μL, 1.0 mmol) were added and the mixture was stirred at room temperature overnight. H2O (15 mL) and CH2Cl2 (10 mL) were added and the aqueous and organic layers were partitioned. The aqueous layer was extracted with CH2Cl2 (1×20 mL), and the combined organic layers were dried over Na2SO4, filtered and the solvent removed under vacuum to leave a crude solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 hr
  3. stirringthe mixture was stirred at room temperature overnight
  4. customthe aqueous and organic layers were partitioned
  5. extractionThe aqueous layer was extracted with CH2Cl2 (1×20 mL)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent removed under vacuum
  9. customto leave a crude solid

Sources & evidence

ORD record
ord-2da36e4956dd46c9b5ba2b47b172a5d8
Source dataset
uspto-grants-2016_09
Patent number
US09439888B2

Reaction notes

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