Lithium Hydroxide → HCID 136027576, compound

HRID 1428839Notes

Reaction equation

HRID 1428839 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[NH:7][C:8]([N:12]3[CH:16]=[C:15]([C:17]([O:19]CC)=[O:18])[CH:14]=[N:13]3)=[N:9]2)=[CH:4][C:3]=1[N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1.[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[NH:7][C:8]([N:12]3[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[N:13]3)=[N:9]2)=[CH:4][C:3]=1[N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 136337167HCID 136337167, compound

Product 1

HCID 136027576HCID 136027576, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[7-chloro-6-(3,4-dihydro-1H-isoquinolin-2-yl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, ethyl ester (0.35 g, 0.78 mmol), THF (12 mL), and aqueous 1M LiOH (7.8 mL, 7.8 mmol) was stirred at rt for 16 h. The THF was removed, and the aqueous mixture was cooled in an ice bath. The pH was adjusted to ca. 5 using 1M aqueous HCl, and the resulting precipitate was collected, washed well with water, and dried to afford the titled compound (0.33 g, 99%). MS (ESI): mass calcd. for C21H16ClN5O3, 421.1; m/z found, 422.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 13.22-12.69 (br m, 2H), 8.92 (s, 1H), 8.25 (s, 1H), 7.88-7.73 (m, 2H), 7.24-7.16 (m, 4H), 4.31 (s, 2H), 3.39 (t, J=5.6, 2H), 3.00 (t, J=5.5, 2H).

Workup

  1. customThe THF was removed
  2. temperaturethe aqueous mixture was cooled in an ice bath
  3. customthe resulting precipitate was collected
  4. washwashed well with water
  5. customdried

Sources & evidence

ORD record
ord-f8ff57fa04624b598e38926a5ab5188b
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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