Hydrochloric Acid → HCID 136262657, compound

HRID 591660Notes

Reaction equation

HRID 591660 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:34])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[CH:17][CH:16]=1)=[N:8]2.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:34])[NH:6][C:7]([C:15]1[CH:16]=[CH:17][C:18]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:19][CH:20]=1)=[N:8]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136262659HCID 136262659, compound

Product 1

HCID 136262657HCID 136262657, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl)piperidine-1-carboxylate (0.210 g, 0.45 mmol) in 1,4-dioxane (2 mL) was added 4M HCl in 1,4-dioxane (1 mL). The resulting solution was stirred at room temperature for 5 hours. Then, the mixture was concentrated in vacuo and the resulting material was purified by flash chromatography on silica gel, eluting with 0% to 10% of MeOH/CH2Cl2. The residue was further purified by flash chromatography on silica gel, eluting with 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH followed by 100% of 6:3:1 CHCl3/MeOH/concentrated NH4OH, to afford the title compound (0.030 g, 18%). 1H NMR (300 MHz, DMSO-d6): δ 8.11 (d, J=8.3 Hz, 2H), 7.37 (d, J=8.2 Hz, 2H), 6.73 (s, 1H), 6.53 (s, 1H), 3.89 (s, 3H), 3.85 (s, 3H), 2.92-3.20 (m, 2H), 2.56-2.81 (m, 3H), 2.35-2.57 (m, 2H), 1.67-1.88 (m, 2H), 1.38-1.67 (m, 2H). ESI MS m/z 366 [M+H]+.

Workup

  1. concentrationThen, the mixture was concentrated in vacuo
  2. customthe resulting material was purified by flash chromatography on silica gel
  3. washeluting with 0% to 10% of MeOH/CH2Cl2
  4. customThe residue was further purified by flash chromatography on silica gel
  5. washeluting with 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH

Sources & evidence

ORD record
ord-650d078477ad4218ab7d7cfbe4b38610
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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