Acetic Acid → HCID 69412878, compound

HRID 851889Notes

Reaction equation

HRID 851889 reaction equation
[O:1]=[S:2]1(=[O:23])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:20][CH2:21][CH2:22][CH:4]2[NH:3]1.CO[CH:26]1[CH2:30][CH2:29][CH:28](OC)O1.O.CC(O)=O>C(Cl)CCl>[N:19]1([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][C:9]2[CH:10]=[CH:11][C:6]3[N:5]4[CH2:20][CH2:21][CH2:22][CH:4]4[NH:3][S:2](=[O:1])(=[O:23])[C:7]=3[CH:8]=2)[CH:26]=[CH:30][CH:29]=[CH:28]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 790982,5-DimethoxytetrahydrofuranHCID 10215256HCID 10215256, compound

Product 1

HCID 69412878HCID 69412878, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

250 mg (0.75 mmol) of {3-[(5,5-dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]-benzothiadiazin-7-yl)oxy]phenyl}amine and 137 μl (1.06 mmol) of 2,5-dimethoxytetra-hydrofuran are added to a two-phase mixture of 2.5 ml of water, 1.25 ml of AcOH and 3.75 ml of dichloro-1,2-ethane. Stirring is carried out at 80° C. for 1 hour; the mixture is allowed to return to ambient temperature and is extracted with CH2Cl2. The organic phase is washed with saturated aqueous NaCl solution and dried over MgSO4. The title product is purified by chromatography on a silica column (CH2Cl2/heptane 70/30).

Workup

  1. customto return to ambient temperature
  2. extractionis extracted with CH2Cl2
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. customThe title product is purified by chromatography on a silica column (CH2Cl2/heptane 70/30)

Sources & evidence

ORD record
ord-8da47214de914282957a396bb259d51f
Source dataset
uspto-grants-2007_08
Patent number
US07253163B2

Reaction notes

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