Dichloromethane → HCID 59993356, compound

HRID 238229Notes

Reaction equation

HRID 238229 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH:13]([NH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:14].C(N(CC)CC)C.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.ClCCl>O1CCOCC1.O>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([S:37]([N:19]2[CH2:20][CH2:21][CH:16]([NH:15][CH:13]([C:3]3[N:2]([CH3:1])[C:11](=[O:12])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]=3)[CH3:14])[CH2:17][CH2:18]2)(=[O:39])=[O:38])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 59993326HCID 59993326, compound

Product 1

HCID 59993356HCID 59993356, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Methyl-2-[1-(piperidin-4-ylamino)-ethyl]-3H-quinazolin-4-one (57.2 mg, 0.2 mmol) and triethylamine (167 μL, 0.4 mmol) were dissolved in dioxane (1 mL) and to this was added 4-methoxybenzenesulfonyl chloride (62 mg, 0.3 mmol). The reaction was shaken at room temperature overnight. Dichloromethane (2 mL) and water (2 mL) were added and the reaction tube was shaken. The top aqueous layer was aspirated off and the organic layer was concentrated in vacuo. The residue was dissolved in DMSO and purified by HPLC to yield the final product, 2-{1-[1-(4-Methoxy-benzenesulfonyl)-piperidin-4-ylamino]-ethyl}-3-methyl-3H-quinazolin-4-one. HPLC ret. time 2.23, 10-99% CH3CN, 5 min run; 1H NMR (CDCl3) δ 1.55 (d, 3H, J=6.6 Hz), 1.66 (q, 2H, J=12.1 Hz), 2.16 (m, 4H), 3.19 (m, 1H), 3.53 (s, 3H), 3.68 (m, 2H), 3.80 (s, 3H), 4.86 (q, 1H, J=5.7 Hz), 7.12 (d, 2H, J=9.0 Hz), 7.57 (t, 1H, J=8.1 Hz), 7.63 (d, 2H, J=8.9 Hz), 7.69 (d, 1H, J=7.7 Hz), 7.86 (t, 1H, J=8.4 Hz), 8.15 (dd, 1H, J=8.0, 1.2 Hz); ESI-MS m/z 457.4 (M+1)+.

Workup

  1. stirringthe reaction tube was shaken
  2. concentrationthe organic layer was concentrated in vacuo
  3. dissolutionThe residue was dissolved in DMSO
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-cae1b03ae6e249038236b7af7cf8d8af
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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