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Diisopropylethylamine → 3-benzyloxy-N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-benzamide

HRID 1844590
Notes
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Reaction equation

HRID 1844590 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.ON1C2N=CC=CC=2N=N1.[CH2:44]([O:51][C:52]1[CH:53]=[C:54]([CH:58]=[CH:59][C:60]=1[CH3:61])[C:55]([OH:57])=O)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.Cl.[NH2:63][C:64]1[C:65]([O:79][CH3:80])=[C:66]([NH:74][S:75]([CH3:78])(=[O:77])=[O:76])[CH:67]=[C:68]([C:70]([CH3:73])([CH3:72])[CH3:71])[CH:69]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:44]([O:51][C:52]1[CH:53]=[C:54]([CH:58]=[CH:59][C:60]=1[CH3:61])[C:55]([NH:63][C:64]1[CH:69]=[C:68]([C:70]([CH3:72])([CH3:73])[CH3:71])[CH:67]=[C:66]([NH:74][S:75]([CH3:78])(=[O:77])=[O:76])[C:65]=1[O:79][CH3:80])=[O:57])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21079205N-(3-amino-5-tert-butyl-2-methoxyphenyl)methanesulphonamide-hydrochlorideHCID 229031883-(Benzyloxy)-4-methylbenzoic acid

Product 1

HCID 67217548
3-benzyloxy-N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

10.59 g of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate, 9.54 ml diisopropylethylamine and 1.26 g 1-hydroxy-7-azabenzotriazole are added to 4.50 g 3-benzyloxy-4-methyl-benzoic acid in 25 ml N,N-dimethylformamide under an argon atmosphere. The mixture is stirred for 15 minutes at ambient temperature, before 5.74 g N-(3-amino-5-tert-butyl-2-methoxyphenyl)methanesulphonamide-hydrochloride are added. The reaction mixture is stirred overnight at 50° C. After cooling to ambient temperature the reaction mixture is diluted with ethyl acetate, washed with water, 1 N hydrochloric acid and saturated aqueous sodium chloride solution, dried on magnesium sulphate and evaporated down. The flask residue is stirred with methanol, and the resulting white precipitate is suction filtered and dried.

Workup

  1. additionare added
  2. temperatureAfter cooling to ambient temperature the reaction mixture
  3. washwashed with water, 1 N hydrochloric acid and saturated aqueous sodium chloride solution
  4. customdried on magnesium sulphate
  5. customevaporated down
  6. stirringThe flask residue is stirred with methanol
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-0ef8f2f3e5bb4b97af5414d0a35b9125
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946438B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes