Triethylamine → HCID 58827248, compound

HRID 448442Notes

Reaction equation

HRID 448442 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[NH2:24][CH2:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:27]=1[C:28](=[O:44])[N:29]([CH:36]1[CH2:41][CH2:40][C:39](=[O:42])[NH:38][C:37]1=[O:43])[C:30]2=[O:35].C(N(CC)CC)C>CN(C=O)C>[O:43]=[C:37]1[CH:36]([N:29]2[C:28](=[O:44])[C:27]3[C:31](=[CH:32][CH:33]=[CH:34][C:26]=3[CH2:25][NH:24][C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)=[O:10])[C:30]2=[O:35])[CH2:41][CH2:40][C:39](=[O:42])[NH:38]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 702826-Methylpyridine-2-carboxylic acidHCID 219885254-(aminomethyl)-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

Product 1

HCID 58827248HCID 58827248, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methylpicolinic acid (0.27 g, 2.0 mmol) and CDI (0.39 g, 2.4 mmol) in DMF (25 mL) was stirred at ambient temperature under nitrogen for 1 hour. 4-Aminomethyl-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione hydrochloride (0.65 g, 2.0 mmol) and triethylamine (0.61 g, 6.0 mmol) were added, and the mixture was allowed to stir for 16 hours. The solvent was evaporated under vacuum, and the residue was purified by preparative HPLC, eluting with 45:55 acetonitrile-water, providing 0.34 g of the product in 54% yield: mp 197-199° C.; 1H NMR (DMSO-d6) δ 2.06-2.11 (m, 1H), 2.53-2.65 (m, 2H), 2.58 (s, 3H), 2.84-2.94 (m, 1H), 4.96 (d, J=6.3 Hz, 2H), 5.18 (dd, J=12.6 Hz, d=5.4 Hz, 1H), 7.49 (dd, J=6.8 Hz, J=1.9 Hz, 1H), 7.69 (dd, J=8.5 Hz, J=4.1 Hz, 1H), 7.79-7.93 (m, 4H), 9.36 (t, J=6.3 Hz, 1H), 11.15 (s, 1H); 13C NMR (DMSO-d6) δ 22.0, 23.9, 30.9, 38.3, 48.9, 119.2, 121.9, 126.3, 127.2, 131.6, 133.0, 134.8, 137.9, 139.2, 149.0, 157.3, 164.5, 167.0, 167.6, 169.8, 172.8; Anal. calcd for C21H18N4O5.0.6H2O: C, 60.45; H, 4.63; N, 13.42. Found: C, 60.47; H, 4.53; N, 13.36.

Workup

  1. stirringto stir for 16 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was purified by preparative HPLC
  4. washeluting with 45:55 acetonitrile-water

Sources & evidence

ORD record
ord-8e2ad2023cd14711b1295cd65b497c4f
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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