Hydrochloric Acid → HCID 178418912, compound

HRID 38185Notes

Reaction equation

HRID 38185 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:12]=2)[NH:8][N:9]=1)=[O:4].[OH-].[Na+].Cl>>[C:3]([C:5]1[CH:6]=[C:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:12]=2)[NH:8][N:9]=1)([OH:4])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178418998HCID 178418998, compound

Product 1

HCID 178418912HCID 178418912, compoundYield 94.2%

Conditions

Temperature
50 °C

Procedure

(5-Methoxycarbonyl-2H-pyrazol-3-yl)-(2-phenyl-quinazolin-4-yl)-amine (III-73) (345 mg, 1 mmole in THF, 6 mL) was treated with NaOH (1M, 4.0 mL), stirred at 50° C. for 5 hours, cooled to room temperature, and neutralised with 1M HCl. The mixture was concentrated in vacuo to remove THF then diluted with water and the resulting precipitate filtered. The residual solid was dried at 80° C. under vacuum to afford III-72 as an off-white solid (312 mg, 94%): mp 289-291° C. (dec.); 1H NMR (DMSO) δ 7.45 (1H, br s), 7.50-7.60 (5H, m), 7.80-7.88 (2H, m), 7.40-7.50 (2H, m), 8.60-8.70 (1H, d), 10.70 (1H, s), 13.00-13.80 (2H, br s); IR (solid) 1699, 1624, 1607, 1570, 1539, 1506, 1486, 1398, 1333, 1256, 1177, 1004, 827, 764, 705; MS 332.3 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. customto remove THF
  4. additionthen diluted with water
  5. filtrationthe resulting precipitate filtered
  6. customThe residual solid was dried at 80° C. under vacuum

Sources & evidence

ORD record
ord-043f25632ff741e0bc277735e1a55333
Source dataset
uspto-grants-2013_09
Patent number
US08524720B2

Reaction notes

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