Hydrochloric Acid → HCID 59784811, compound

HRID 470325Notes

Reaction equation

HRID 470325 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH2:27])=[N:8][N:9]([C:11]2[N:20]=[CH:19][C:18]3[CH2:17][CH2:16][C:15]4[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:14]=4[C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[Na+].CO.Cl>O>[NH2:27][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:10][N:9]([C:11]2[N:20]=[CH:19][C:18]3[CH2:17][CH2:16][C:15]4[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:14]=4[C:13]=3[N:12]=2)[N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59785001HCID 59785001, compound

Product 1

HCID 59784811HCID 59784811, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-Amino-1-(8-methoxy-5,6-dihydro-benzo[h]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester(3, 3.15 g, 8.63 mM), 1 N NaOH (15 mL), and methanol (20 mL) was heated at 100° C. for 3 hr then cooled to room temperature and diluted with water (100 mL). the pH was adjusted with 1 N HCl to approximately 3-4 and the resulting precipitate was isolated via filtration, washed with water (2×80 mL) and dried in vaccuo to give 3-Amino-1-(8-methoxy-5,6-dihydro-benzo[h]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid (4, 3.02 g, 100% yield). ES-MS MH+ 338.4 1H NMR (300 MHz, ppm, DMSO-d6): 8.81 (s, 1H), 8.57 (s, 1H), 8.2 (d, 1H), 7.0 (dd, 1H), 6.95 (s, 1H), 3.85 (s, 3H), 2.93 (m, 4H).

Workup

  1. temperaturethen cooled to room temperature
  2. customthe resulting precipitate was isolated via filtration
  3. washwashed with water (2×80 mL)
  4. customdried in vaccuo

Sources & evidence

ORD record
ord-eef13bc1c12a4e7e98c14a6e48d84d42
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

Loading…