Hydrochloric Acid → HCID 136337191, compound

HRID 1428886Notes

Reaction equation

HRID 1428886 reaction equation
Cl.O1CCOCC1.[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:18]2[N:27](COCCOC)[C:26](=[O:34])[C:25]3[C:20](=[CH:21][C:22]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:23][CH:24]=3)[N:19]=2)[CH:17]=1)=[O:12])[CH3:9]>>[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:18]2[NH:27][C:26](=[O:34])[C:25]3[C:20](=[CH:21][C:22]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:23][CH:24]=3)[N:19]=2)[CH:17]=1)=[O:12])[CH3:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68488561HCID 68488561, compound

Product 1

HCID 136337191HCID 136337191, compoundYield 53%

Conditions

Temperature
23 °C

Procedure

A solution of 4M HCl and dioxane (3.00 mL, 12.0 mmol) was added to 1-[3-(2-methoxy-ethoxymethyl)-4-oxo-7-phenyl-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (90.0 mg, 0.201 mmol). The reaction mixture was stirred at 23° C. After 18 h, the reaction mixture was concentrated under reduced pressure. Et2O was added (5 mL) and the resulting precipitate was collected by filtration and washed well with Et2O to afford the titled compound (38.0 mg, 53%). MS (ESI): mass calcd. for C20H16N4O3, 360.1; m/z found, 361.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 12.93 (s, 1H), 9.04 (s, 1H), 8.34 (s, 1H), 8.20 (d, J=8.2 Hz, 1H), 7.98 (s, 1H), 7.84 (dd, J=10.5, 4.2 Hz, 3H), 7.55 (t, J=7.6 Hz, 2H), 7.49-7.46 (m, 1H), 4.31 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEt2O was added (5 mL)
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed well with Et2O

Sources & evidence

ORD record
ord-9fa7edfafff04ce984fe4813347fe65a
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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