Propionyl chloride → HCID 21988533, compound

HRID 718716Notes

Reaction equation

HRID 718716 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:10](=[O:11])[N:9]([CH:12]3[C:18](=[O:19])[NH:17][C:15](=[O:16])[CH2:14][CH2:13]3)[CH2:8][C:4]2=[C:5]([NH2:7])[CH:6]=1.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>N1C=CC=CC=1>[O:19]=[C:18]1[CH:12]([N:9]2[CH2:8][C:4]3[C:3](=[CH:2][CH:1]=[CH:6][C:5]=3[NH:7][C:20](=[O:23])[CH2:21][CH3:22])[C:10]2=[O:11])[CH2:13][CH2:14][C:15](=[O:16])[NH:17]1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 216326Lenalidomide

Product 1

HCID 21988533HCID 21988533, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of lenalidomide (0.020 g, 0.077 mmol) in pyridine (0.8 mL) was cooled to 0° C. (ice bath). Propionyl chloride (0.009 mL, 0.100 mmol) was added dropwise and the reaction was allowed to warm to room temperature over 16 h. Volatiles were removed in vacuo and the crude residue was purified by flash chromatography on silica gel (0→5% MeOH in DCM as eluant) to afford desired product 27 (0.012 g, 50%) as an off-white powder. 1H NMR (400 MHz, DMSO) δ 11.04 (s, 1H), 9.79 (s, 1H), 7.80 (dd, J=6.6, 2.3 Hz, 1H), 7.64-7.29 (m, 2H), 5.14 (dd, J=13.2, 4.9 Hz, 2H), 4.35 (q, J=7.5 Hz, 2H), 3.00-2.79 (m, 1H), 2.60 (m, 1H), 2.35 (m, 1H), 2.05-1.92 (m, 1H), 1.08 (t, J=7.5 Hz, 3H). MS (ESI) m/z calcd for C16H18N3O4 [M+H]+ 316.3, found: 316.8.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe crude residue was purified by flash chromatography on silica gel (0→5% MeOH in DCM as eluant)

Sources & evidence

ORD record
ord-e82223d9bee843fcac61256db4ae491c
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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