Thiourea → HCID 89964828, compound

HRID 1846208Notes

Reaction equation

HRID 1846208 reaction equation
ClCC([NH:5][C:6]1([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[O:9][CH2:8][CH2:7]1)=O.NC(N)=S>CCO.CC(O)=O.CCOC(C)=O>[F:26][C:23]([F:24])([F:25])[O:22][C:19]1[CH:20]=[CH:21][C:16]([C:6]2([NH2:5])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[O:9][CH2:8][CH2:7]2)=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 2723790ThioureaHCID 89964983HCID 89964983, compound

Product 1

HCID 89964828HCID 89964828, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-chloro-N-(4-(4-(trifluoromethoxy)phenyl)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)acetamide (1.5 g, 3.8 mmol) in EtOH (5 times) and AcOH (cat.), was added thiourea (0.3 g, 4.2 mmol). The reaction was stirred at 60° C. for 12 h. The progress of reaction was monitored by TLC (50% EtOAc in petroleum ether). The reaction was diluted with EtOAc (10 mL) and quenched slowly with saturated NaHCO3 (25 mL). The aqueous layer was extracted with EtOAc (10 mL). The combined organic layers were washed with brine (10 mL), dried over MgSO4, and concentrated to give the product as a residue. Purification by column chromatography (60-120 mesh silica, 0-50% EtOAc/hexanes) gives the title compound as a brown oil. MS (ESI pos. ion) m/z: 294.1 (M-NH2). 1H NMR (300 MHz, CDCl3): δ 8.2 (d, J=4.0 Hz, 1H), 7.3 (m, 2H), 7.1-7.2 (m, 4H), 4.3 (m, 1H), 4.0 (m, 1H), 2.35-2.45 (m, 2H).

Workup

  1. customThe progress of reaction
  2. customquenched slowly with saturated NaHCO3 (25 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (10 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give the product as a residue
  8. customPurification by column chromatography (60-120 mesh silica, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b1c1fb0857c54b6199e29667557a2409
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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