Diisopropylethylamine → HCID 178509500, compound

HRID 606377Notes

Reaction equation

HRID 606377 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([S:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][NH2:17])[CH:13]=[CH:14][CH:15]=2)=[N:2]1.[C:18]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([C:30](OCC)=[O:31])[NH:24][C:23]2=[O:35])#[N:19].C(N(C(C)C)CC)(C)C>C(O)C>[C:18]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([C:30]([NH:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][CH2:7][S:6][C:3]3[N:4]=[CH:5][NH:1][N:2]=3)[CH:11]=1)=[O:31])[NH:24][C:23]2=[O:35])#[N:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 136054489Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylateHCID 178509870HCID 178509870, compound

Product 1

HCID 178509500HCID 178509500, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 1-(3-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}phenyl)methanamine obtained in Reference Example 3 (300 mg, 0.999 mmol), ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate obtained in Reference Example 51 (200 mg, 0.822 mmol) and diisopropylethylamine (0.180 mL, 1.05 mmol) in ethanol (2 mL) was stirred at 90° C. for 2 days. The reaction solvent was evaporated under reduced pressure, and the residue was purified by preparative HPLC (GILSON 215LIQUD HANDLER, 322PUMP, UV/VIS-156, SHISEIDO CAPCELL PACK C-18 UG120 S-5 (20 mmφ×50 mm), mobile phase: distilled water (containing 0.1% trifluoroacetic acid)/acetonitrile (containing 0.1% trifluoroacetic acid), gradient: distilled water/acetonitrile=90/100/100, time: 10 min, flow rate: 25 mL/min, detection wavelength: 220 nm), and the obtained crude crystals were recrystallized from ethanol to give the title compound as a white powder (97.4 mg, 26%).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure
  2. customthe residue was purified by preparative HPLC (GILSON 215LIQUD HANDLER, 322PUMP, UV/VIS-156, SHISEIDO CAPCELL PACK C-18 UG120 S-5 (20 mmφ×50 mm), mobile phase
  3. distillationdistilled water (containing 0.1% trifluoroacetic acid)/acetonitrile (containing 0.1% trifluoroacetic acid)
  4. distillationgradient: distilled water/acetonitrile=90/100/100, time
  5. custom10 min, flow rate: 25 mL/min, detection wavelength: 220 nm), and the obtained crude crystals
  6. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-db23ea09ac0b423195921f132b6f0c90
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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