Acetic Acid → 7-[3-(1H-Pyrrol-1-ylmethyl)phenoxy]-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

HRID 29772Notes

Reaction equation

HRID 29772 reaction equation
Cl.[O:2]=[S:3]1(=[O:25])[C:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH2:20][NH2:21])[CH:17]=[CH:18][CH:19]=3)[CH:11]=[CH:12][C:7]=2[N:6]2[CH2:22][CH2:23][CH2:24][CH:5]2[NH:4]1.CO[CH:28]1[CH2:32][CH2:31][CH:30](OC)O1.O.CC(O)=O>C(Cl)CCl>[N:21]1([CH2:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[O:13][C:10]2[CH:11]=[CH:12][C:7]3[N:6]4[CH2:22][CH2:23][CH2:24][CH:5]4[NH:4][S:3](=[O:2])(=[O:25])[C:8]=3[CH:9]=2)[CH:28]=[CH:32][CH:31]=[CH:30]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 790982,5-DimethoxytetrahydrofuranHCID 69197863HCID 69197863, compound

Product 1

HCID 691987587-[3-(1H-Pyrrol-1-ylmethyl)phenoxy]-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

200 mg (0.58 mmol) of the product obtained in Example 1, in the form of the free amine, and 105 μl (0.81 mmol) of 2,5-dimethoxytetrahydrofuran are added to a two-phase mixture of 2.5 ml of water, 0.95 ml of AcOH and 2.85 ml of dichloro-1,2-ethane. The mixture is stirred at 80° C. for 2 hours, allowed to return to ambient temperature and extracted with CH2Cl2. The organic phase is washed with saturated aqueous NaCl solution and dried over MgSO4. The expected product is purified by chromatography on a silica column (CH2Cl2/heptane 75/25).

Workup

  1. customto return to ambient temperature
  2. extractionextracted with CH2Cl2
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. customThe expected product is purified by chromatography on a silica column (CH2Cl2/heptane 75/25)

Sources & evidence

ORD record
ord-193c00d47d504ab2bdf9af6b0c39ec60
Source dataset
uspto-grants-2008_09
Patent number
US07423034B2

Reaction notes

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