Hydrochloric Acid → HCID 59205166, compound

HRID 2061427Notes

Reaction equation

HRID 2061427 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[N:3]=1.[NH2:21][C:22]1[CH:30]=[CH:29][C:28]2[CH2:27][CH2:26][CH2:25][C:24]=2[C:23]=1[S:31]([NH2:34])(=[O:33])=[O:32].Cl>C(O)(C)C>[CH3:20][O:19][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[N:3]=[C:2]([NH:21][C:22]3[CH:30]=[CH:29][C:28]4[CH2:27][CH2:26][CH2:25][C:24]=4[C:23]=3[S:31]([NH2:34])(=[O:32])=[O:33])[CH:7]=[CH:6][N:5]=2)[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57751017HCID 57751017, compoundHCID 58154431HCID 58154431, compound

Product 1

HCID 59205166HCID 59205166, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(4-Chloro-pyrimidin-2-yl)-(3,4,5-trimethoxy-phenyl)-amine (240 mg, 0.81 mmol) and 5-amino-indan-4-sulfonic acid amide (190 mg, 0.89 mmol) are suspended in isopropanol (15 ml). Conc. HCl (1.5 ml) is added. The mixture is heated to reflux for 1 h. The reaction mixture is separated between ethyl acetate (300 ml) and water (100 ml). NaHCO3 is added to achieve basic pH. The layers are separated. The organic layer is dried with Na2SO4 and evaporated. The residue is crystallized from ethyl acetate to give 5-[2-(3,4,5-trimethoxy-phenylamino)-pyrimidin-4-ylamino]-indan-4-sulfonic acid amide.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 h
  3. customThe reaction mixture is separated between ethyl acetate (300 ml) and water (100 ml)
  4. additionNaHCO3 is added
  5. customThe layers are separated
  6. dry with materialThe organic layer is dried with Na2SO4
  7. customevaporated
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e108b471b58b4c94aa47458a14565e1d
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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