N,N-Dimethylglycine → HCID 24968655, compound

HRID 1868262Notes

Reaction equation

HRID 1868262 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([OH:7])=O)[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:21][CH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[C:25](=[O:42])[N:26]([CH:34]1[CH2:39][CH2:38][C:37](=[O:40])[NH:36][C:35]1=[O:41])[C:27]([CH3:33])=[N:28]2>CN(C=O)C>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]([NH:21][CH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[C:25](=[O:42])[N:26]([CH:34]1[CH2:39][CH2:38][C:37](=[O:40])[NH:36][C:35]1=[O:41])[C:27]([CH3:33])=[N:28]2)=[O:7]

Participants

5

Reactant 3

HCID 673N,N-DimethylglycineHCID 682631,1'-CarbonyldiimidazoleHCID 249683051015474-47-1

Product 1

HCID 24968655HCID 24968655, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of dimethylamino-acetic acid (0.27 g, 1.9 mmol) in DMF in a 40° C. oil bath (8 mL), was added 1,1′ carbonyldiimidazole (0.35 g, 2.1 mmol) and stirred for one hour. Then 3-(5-aminomethyl-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione hydrogen chloride (0.65 g, 1.9 mmol) was added and stirred for 15 minutes. The solvent was evaporated, and the residue was purified by flash column chromatography (Silica gel, methanol/methylene chloride 4%/96%) to give 2-dimethylamino-N-[3-(2,6-dioxo-piperidin-3-yl)-2-methyl-4-oxo-3,4-dihydro-quinazolin-5-ylmethyl]-acetamide as a light yellow solid (340 mg, 46% yield); HPLC, Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 05/95 CH3CN/0.1% H3PO4, 7.29 min (99.8%); mp, 275° C. (decomposed); 1HNMR (DMSO-d6) 2.16-2.19 (m, 7H, CHH and NMe2), 2.63-2.91 (m, 8H, CHCH2, CH3 and NCH2), 4.74-4.76 (m, 2H, CH2NH), 5.25 (dd, J=6, 12 Hz, 1H, CH), 7.31-7.76 (m, 3H, Ar), 8.26 (t, J=6 Hz, 1H, CH2NH), 11.03 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.68, 23.31, 30.59, 41.62, 45.54, 56.51, 62.81, 117.69, 125.53, 125.74, 133.96, 140.54, 148.52, 154.82, 161.03, 169.42, 169.63, 172.63. LCMS MH=386; Anal Calcd For C19H23N5O4: C, 59.21; H, 6.01; N, 18.17. Found: C, 58.95; H, 6.05; N, 17.79.

Workup

  1. stirringstirred for 15 minutes
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash column chromatography (Silica gel, methanol/methylene chloride 4%/96%)

Sources & evidence

ORD record
ord-74f485344a5f4ac29d486a7dbdb8246c
Source dataset
uspto-grants-2009_12
Patent number
US07635700B2

Reaction notes

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