Sodium Bicarbonate → HCID 68109125, compound

HRID 2179363Notes

Reaction equation

HRID 2179363 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:23][C:22]4[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].CO.[ClH:38]>>[ClH:38].[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:23][C:22]4[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 68109053HCID 68109053, compound

Product 1

HCID 68109125HCID 68109125, compound

Procedure

The product of step F (22 mg, 0.05 mmol) in 2N HCl diethyl ether solution (5 mL) was stirred at 0-5° C. for 2 h and then at ambient temperature for 4 h. After concentration in vacuo, the solid obtained was treated with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude material which was purified by flash column chromatography (SiO2, 80:18:2 dichloromethane/methanol/ammonium hydroxide) followed by semi-preparative HPLC. After concentration in vacuo, the solid obtained was treated with 1.25M HCl methanol solution (0.5 mL) and lyophilized to yield 9-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzofuro[3,2-c]azepine hydrochloride (2.8 mg, 15%, AUC HPLC 98.8%) as a white solid: mp 211-216° C.; 1H NMR (CD3OD, 300 MHz) δ 8.12 (s, 1H), 7.96 (dt, J=6.6, 1.8 Hz, 2H), 7.81 (dd, J=8.7, 1.8 Hz, 1H), 7.76-7.51 (m, 4H), 4.02 (s, 2H), 3.19 (br s, 2H), 3.05 (t, J=6.0 Hz, 2H), 1.95 (br s, 2H); ESI MS m/z 328 [M+H]+.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe solid obtained
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material which
  8. customwas purified by flash column chromatography (SiO2, 80:18:2 dichloromethane/methanol/ammonium hydroxide)
  9. concentrationAfter concentration in vacuo
  10. customthe solid obtained

Sources & evidence

ORD record
ord-a0696c13161a4b12baf6a104845af86d
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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