Dimethyl Sulfoxide → Pomalidomide

HRID 718725Notes

Reaction equation

HRID 718725 reaction equation
CS(C)=O.Cl.[NH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:30])[N:10]([C:17]1(CCCCN)[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]1=[O:24])[C:11]2=[O:16].C(N(CC)CC)C.C(CN)O>C(O)(C)C>[CH:14]1[CH:13]=[C:12]2[C:11](=[O:16])[N:10]([CH:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[CH2:21][CH2:22]3)[C:9](=[O:30])[C:8]2=[C:7]([NH2:6])[CH:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 700EthanolamineHCID 8471Triethylamine2×HCID 67997624HCID 67997624, compound

Product 1

HCID 134780Pomalidomide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

About 2 mL of a suspension of affigel-10 (15 μmol/mL of gel, 50% slurry) in isopropanol was transferred to a conical tube and centrigured to a settled volume of 1.04 mL. The isopropanol was removed and the affigel-10 was washed with DMSO (3×5 mL). A DMSO (2.2 mL) solution of 7 (0.002 g, 0.00525 mmol) and triethylamine (0.007 mL, 0.0525 mmol) was subsequently added and the resulting mixture was sealed and tumbled on a rotator at room temperature. After 16 h, the conical tube was spun down and the DMSO supernatant was tested for the presence of 7 by LC-MS. 7 was not observed and therefore to the mixture was added triethylamine (0.015 mL, 0.105 mmol) and ethanolamine (0.006 mL, 0.10503 mmol) and the resulting mixture was tumbled on a rotator at room temperature. After 20 h, SS-0007896 was spun down, the solvent was removed, and the resin was washed with DMSO (3×5 mL) and isopropanol (3×5 mL) and stored in isopropanol at −20° C.

Workup

  1. customThe isopropanol was removed
  2. washthe affigel-10 was washed with DMSO (3×5 mL)
  3. customthe resulting mixture was sealed
  4. customtumbled on a rotator at room temperature
  5. customwas tumbled on a rotator at room temperature
  6. waitAfter 20 h
  7. customthe solvent was removed
  8. washthe resin was washed with DMSO (3×5 mL) and isopropanol (3×5 mL)
  9. customstored in isopropanol at −20° C.

Sources & evidence

ORD record
ord-24c3fc73273746debc11ad580ba0c6ea
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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