Lithium hydroxide, monohydrate → HCID 57335331, compound

HRID 517468Notes

Reaction equation

HRID 517468 reaction equation
[CH3:1][N:2]([CH3:46])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:45])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:29]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[C:27]4[C:22](=[CH:23][C:24]([C:36]5[O:40][C:39]([C:41]([O:43]C)=[O:42])=[CH:38][CH:37]=5)=[CH:25][CH:26]=4)[N:21]=3)=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)=[O:4].O.[OH-].[Li+]>CO.C1COCC1.O>[CH3:1][N:2]([CH3:46])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:45])[NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[N:29]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[C:27]4[C:22](=[CH:23][C:24]([C:36]5[O:40][C:39]([C:41]([OH:43])=[O:42])=[CH:38][CH:37]=5)=[CH:25][CH:26]=4)[N:21]=3)=[CH:18][CH:19]=2)=[CH:9][CH:10]=1)=[O:4]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67514051HCID 67514051, compound

Product 1

HCID 57335331HCID 57335331, compoundYield 61.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a 100 mL round bottom flask, methyl 5-(2-(4-(3-(4-(dimethylcarbamoyl)phenyl)ureido)phenyl)-4-morpholino-quinazolin-7-yl)furan-2-carboxylate (0.1 g, 0.00016 mol) in MeOH (2 mL), THF (2 mL) and water (2 mL) was added. Subsequently, lithium hydroxide monohydrate (0.034 g, 0.0008 mol) was added and stirred at 25° C. for 12 h. The volatiles were evaporated under reduced pressure, the residue redissolved in water and acidified with 2 N HCl to obtain a pH of 5.0. The volatiles were evaporated under reduced pressure and the residue was stirred with water and filtered. The obtained solid was washed with MeOH to yield the title compound [0.06 g, 61%]. 1H NMR (300 MHz, DMSO-d6): δ 12.12 (s, 1H), 8.57 (s, 1H), 8.54 (s, 1H), 8.25 (s, 1H), 8.05 (d, J=9.0 Hz, 2H), 7.97 (d, J=7.5 Hz, 2H), 7.87 (d, J=8.4 Hz, 1H), 7.79 (d, J=8.4 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H), 7.28 (s, 2H), 7.04 (s, 1H), 3.85 (s, 8H), 2.98 (s, 6H). LC-MS (ESI): Calculated mass: 606.2; Observed mass: 607.2 (RT: 0.63 min).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. dissolutionthe residue redissolved in water
  3. customto obtain a pH of 5.0
  4. customThe volatiles were evaporated under reduced pressure
  5. stirringthe residue was stirred with water
  6. filtrationfiltered
  7. washThe obtained solid was washed with MeOH

Sources & evidence

ORD record
ord-7583603d19bb4b0394fd8ccbd24a202b
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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