Dimethylamine → HCID 58827242, compound

HRID 448414Notes

Reaction equation

HRID 448414 reaction equation
[O:1]=[C:2]1[CH:7]([N:8]2[C:16](=[O:17])C3C(=CC=CC=3NCC(O)=O)[C:9]2=[O:23])[CH2:6][CH2:5][C:4](=[O:24])[NH:3]1.[CH:25]1[CH:26]=[CH:27][C:28]2N(O)N=[N:31][C:29]=2[CH:30]=1.C1CCN2[C:38](=[N:39][CH2:40]CC2)[CH2:37]C1.CNC.CN(C=[O:53])C>C(Cl)Cl.C(O)C>[O:1]=[C:2]1[CH:7]([N:8]2[C:9](=[O:23])[C:28]3[C:27](=[CH:26][CH:25]=[CH:30][C:29]=3[NH:31][CH2:37][C:38]([NH:39][CH3:40])=[O:53])[C:16]2=[O:17])[CH2:6][CH2:5][C:4](=[O:24])[NH:3]1

Participants

8

Reactant 5

HCID 674DimethylamineHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58827328N-[2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]glycine

Product 1

HCID 58827242HCID 58827242, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylamino]acetic acid (0.73 g, 2.2 mmol) in DMF (20 mL), were successively added HOBt (0.32 g, 2.4 mmol), DBU (0.38 g, 2.5 mmol), dimethylamine (90 mg, 2 mmol) and EDC-Cl (0.58 g, 3.0 mmol). The solution was stirred overnight at room temperature. The solvent was evaporated in vacuo, giving a yellow oil. The oil was dissolved in CH2Cl2 (200 mL), washed with water (3×100 mL) and brine (100 mL), and dried (MgSO4). The solvent was evaporated in vacuo to give a yellow solid. Following an ethanol trituration, the resulting solid was purified by preparative HPLC, giving 0.52 g of the product in 73% yield: mp 239-241° C.; 1H NMR (DMSO-d6) δ 2.02-2.06 (m, 1H), 2.47-2.63 (m, 2H), 2.83-3.01 (m, 7H), 4.15 (d, J=3.9 Hz, 2H), 5.08 (dd, J=12.6 Hz, J=5.3 Hz, 1H), 7.05-7.10 (m, 3H), 7.60 (t, J=8.1 Hz, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6) δ 22.12, 30.96, 35.04, 35.34, 45.53, 48.55, 109.48, 110.72, 118.13, 131.98, 136.12, 145.36, 167.31, 167.59, 168.75, 170.02, 172.76; Anal. calcd. for C17H18N4O5.0.3H2O: C, 56.13; H, 5.15; N, 15.40. Found: C, 56.17; H, 5.15; N, 15.26.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customgiving a yellow oil
  3. washwashed with water (3×100 mL) and brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customto give a yellow solid
  7. customthe resulting solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-604099d0b0a341bca3b53025396696d9
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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