Triethylamine → HCID 19047043, compound

HRID 1780594Notes

Reaction equation

HRID 1780594 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=2)[CH:3]=1.C(N(CC)CC)C.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:28]([CH:25]2[CH2:27][CH2:26]2)=[O:29])=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:14]([F:15])([F:17])[F:16])[N:13]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 19047040HCID 19047040, compound

Product 1

HCID 19047043HCID 19047043, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the product obtained in Step E (0.46 g, 1.8 mmol) and triethylamine (250 μL, 1.8 mmol) in anhydrous tetrahydrofuran (THF, 15 mL) cooled to 0° C. was added dropwise a solution of cyclopropanecarbonyl chloride (160 μL, 1.8 mmol) in THF (5 mL). The mixture was stirred at 0° C. for 30 min and then at room temperature overnight. The reaction mixture was filtered and the solids were washed with ethyl acetate. The filtrate was evaporated to dryness and the residue purified by recrystallization from hexane to yield 0.41 g (71% yield) of the title compound as a white solid melting at 155°-156° C. 1H NMR (400 MHz, CDCl3) δ 11.75 (s,1H), 8.61-8.63 (m,1H), 7.76 (s, 1H), 7.55 (s,1H), 7.26-7.27 (m,1H), 2.37 (s,3H), 1.56-1.62 (m,2H), 1.07-1.13 (m,2H).

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe reaction mixture was filtered
  4. washthe solids were washed with ethyl acetate
  5. customThe filtrate was evaporated to dryness
  6. customthe residue purified by recrystallization from hexane

Sources & evidence

ORD record
ord-421993c59330403cbd79a4c76e745f72
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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