Hydrochloric Acid → HCID 68108369, compound

HRID 2179384Notes

Reaction equation

HRID 2179384 reaction equation
[C:1]1([C:7](C2C=CC=CC=2)=[N:8][NH:9][C:10]2[C:15]3[O:16][C:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C:18]=4[C:14]=3[CH:13]=[C:12]([S:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:11]=2)[CH:6]=CC=CC=1.COC(OC)CC(OC)OC.Cl>C(O)C>[C:33]1([S:30]([C:12]2[CH:11]=[C:10]([N:9]3[CH:6]=[CH:1][CH:7]=[N:8]3)[C:15]3[O:16][C:17]4[CH2:22][CH2:21][NH:20][CH2:19][C:18]=4[C:14]=3[CH:13]=2)(=[O:31])=[O:32])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66019TetramethoxypropaneHCID 86668001HCID 86668001, compound

Product 1

HCID 68108369HCID 68108369, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product of step B (65 mg, 0.10 mmol), 1,1,3,3-tetramethoxypropane (18 μL, 0.11 mmol) and concentrated HCl (0.25 mL) was dissolved in ethanol (5 mL). The reaction flask was purged with argon, sealed and heated at 100° C. for 5 h. The reaction mixture was cooled to ambient temperature, quenched with 10% sodium bicarbonate solution, and extracted with dichloromethane. The organic extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 93:7 dichloromethane/methanol) to give 8-(phenylsulfonyl)-6-(1H-pyrazol-1-yl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (23 mg, 56%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.48 (dd, J=2.8, 0.4 Hz, 1H), 8.43 (d, J=1.6 Hz, 1H), 8.03-7.97 (m, 2H), 7.93 (d, J=1.6 Hz, 1H), 7.82-7.77 (m, 1H), 7.58-7.45 (m, 3H), 6.53 (dd, J=2.4, 2.0 Hz, 1H), 4.01 (t, J=2.0 Hz, 2H), 3.27 (t, J=5.6 Hz, 2H), 2.90-2.81 (m, 2H).

Workup

  1. customThe reaction flask was purged with argon
  2. customsealed
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. customquenched with 10% sodium bicarbonate solution
  5. extractionextracted with dichloromethane
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography (SiO2, 93:7 dichloromethane/methanol)

Sources & evidence

ORD record
ord-fe4de1ce752447f9b6e546a54e5484c5
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…