Hydrochloric Acid → HCID 25191224, compound

HRID 388457Notes

Reaction equation

HRID 388457 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][C:5]1([CH2:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:23][C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][C:31]=4[CH3:33])[N:26]([CH3:34])[CH:25]=3)[C:13]2=[O:35])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.Cl>O1CCOCC1.O>[CH3:34][N:26]1[C:27]2[C:32](=[C:31]([CH3:33])[CH:30]=[CH:29][CH:28]=2)[C:24]([CH2:23][N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21](=[O:22])[N:12]([CH2:11][C:5]3([CH2:4][C:3]([OH:36])=[O:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]3)[C:13]2=[O:35])=[CH:25]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68745057HCID 68745057, compound

Product 1

HCID 25191224HCID 25191224, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of {1-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl]-cyclohexyl}-acetic acid methyl ester (63 mg, 0.13 mmol) in dioxane (2.5 ml) is added a solution of LiOH monohydrate (25 mg, 0.60 mmol) in H2O (2.5 mL). The solution is stirred at 60° C. for 16 hours. The reaction mixture is allowed to cool to room temperature, quenches with 4M HCl in dioxane (500 μL) and is concentrated. The resulting residue is purified by flash chromatography with 6% MeOH in dichloromethane as the eluent to afford the title compound. LCMS (ESMS): m/z 474.18 (M+H+)

Workup

  1. temperatureto cool to room temperature
  2. concentrationis concentrated
  3. customThe resulting residue is purified by flash chromatography with 6% MeOH in dichloromethane as the eluent

Sources & evidence

ORD record
ord-18dc683cd747413f99f6a77c7e604df6
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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