Triethylamine → 2,3-Dihydro-3-thioxo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindol-1-one

HRID 1009090Notes

Reaction equation

HRID 1009090 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[S:11])[N:3]1[CH:12]([CH2:17][CH2:18][C:19]([O:21]C)=O)[C:13](OC)=[O:14].FC(F)(F)C([NH2:27])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(Cl)Cl.O>[S:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH:12]1[CH2:17][CH2:18][C:19](=[O:21])[NH:27][C:13]1=[O:14]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 67717TrifluoroacetamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11404450HCID 11404450, compound

Product 1

HCID 113916772,3-Dihydro-3-thioxo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindol-1-oneYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of compound 208 (81 mg, 0.276 mmol), trifluoroacetamide (57 mg, 0.50 mmol), 1-hydroxybenzotriazole (145 mg, 1.07 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (200 mg, 1.04 mmol) and triethylamine (0.21 mL, 1.51 mmol) in CH2Cl2 (1.5 mL) was stirred at ambient temperature for 3 days. Water (10 mL) and CH2Cl2 (10 mL) were added. The dichloromethane layer was separated, washed with water, dried over Na2SO4 and evaporated under reduced pressure. Purification by chromatography, with EtOAc:CH2Cl2 (1:10) as the eluent, gave compound 212 (48 mg, 63%) as a red solid: mp 255° C.; 1H NMR (CDCl3) δ 8.00-7.98 (m, 1H), 7.80-7.71 (m, 3H), 5.63 (br, 1H), 2.98-2.70 (m, 3H), 2.18-2.15 (m, 1H); MS (CI/CH4) m/z 274 (M+); Anal. (C13H10N2O3S) C, H, N.

Workup

  1. customThe dichloromethane layer was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-176602f6edd34361bc733b3e6f8f1c19
Source dataset
uspto-grants-2011_07
Patent number
US07973057B2

Reaction notes

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