Hydrochloric Acid → HCID 9850898, compound

HRID 1066520Notes

Reaction equation

HRID 1066520 reaction equation
[Na].[CH3:2][O:3][C:4]([C:6]1[CH:11]=[C:10]([C:12]2[N:17]=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=3)(=[O:21])=[O:20])[C:15]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:14]([O:40][CH3:41])[N:13]=2)[CH:9]=[CH:8][N:7]=1)=N.Cl.CC[O:45]C(C)=O.O>CO>[CH3:2][O:3][C:4]([C:6]1[CH:11]=[C:10]([C:12]2[N:17]=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=3)(=[O:20])=[O:21])[C:15]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:14]([O:40][CH3:41])[N:13]=2)[CH:9]=[CH:8][N:7]=1)=[O:45]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 69289426HCID 69289426, compound

Product 1

HCID 9850898HCID 9850898, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.586 g of 4-[4-(5-isopropyl-pyridine-2-sulfonylamino)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carboximidic acid methyl ester sodium salt, product of example 41 c), in methanol (10 ml) were added 6 N HCl (3 ml) and the mixture was refluxed for 1 h until the reaction was complete according to TLC analysis (eluent: CH2CL2/EtOAc: 4/1). The mixture was poured into water and the product extracted into EtOAc. The organic layer was washed with water, dried over Na2SO4 and the solvent removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with Me2Cl2/EtOAc: 4/1). Combination of the purified fractions and evacuation in vacuo afforded 4-[4-(5-isopropyl-pyridine-2-sulfonylamino)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carboxylic acid methyl ester as an off-white solid. ISN mass spectrum, m/e 564.2 (M−1 calculated for C27H27N5O7S: 564).

Workup

  1. temperaturethe mixture was refluxed for 1 h until the reaction
  2. extractionthe product extracted into EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customThe residue was purified on a silica gel chromatography column (eluted with Me2Cl2/EtOAc: 4/1)

Sources & evidence

ORD record
ord-98efe69d35804cd0a57e593da32bd9fb
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

Loading…