Ammonium Chloride → HCID 18931097, compound

HRID 1599025Notes

Reaction equation

HRID 1599025 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:30][CH2:31][CH2:32][O:33][CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][O:35]3)[N:18]=[C:17](S(C)(=O)=O)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:44][N:45]([CH2:47][CH2:48][NH2:49])[CH3:46].[Cl-].[NH4+]>CS(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:30][CH2:31][CH2:32][O:33][CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][O:35]3)[N:18]=[C:17]([NH:49][CH2:48][CH2:47][N:45]([CH3:46])[CH3:44])[N:16]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66053N,N-DimethylethylenediamineHCID 18931062HCID 18931062, compound

Product 1

HCID 18931097HCID 18931097, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

##STR143## (1) A mixture of 4-tert-butyl-N-{5-(2-methoxyphenoxy)-2-methylsulfonyl-6-[2-(tetrahydropyran-2-yloxy)ethoxy]pyrimidin-4-yl}benzenesulfonamide obtained in Reference Example 10-(2) (200 mg), dimethylaminoethylamine (138.8 mg) and dimethylsulfoxide (1 ml) is reacted at 100° C. for 15 hours, and then reacted at 120° C. for five hours. The reaction mixture is treated with ammonium chloride, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated under reduced pressure. The residue is purified by preparative silica gel thin layer chromatography (solvent; chloroform:methanol=10:1) to give 4-tert-butyl-N-{2-(2-(N,N-dimethylamino)-ethylamino)-5-(2-methoxyphenoxy)-6-[2-(tetrahydropyran-2-yloxy)ethoxy]-pyrimidin-4-yl}benzenesulfonamide (99.7 mg) as a crystal.

Workup

  1. customis reacted at 100° C. for 15 hours
  2. customreacted at 120° C. for five hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue is purified by preparative silica gel thin layer chromatography (solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-b8cd9bef62a7433cba750faf5b1f1426
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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