Hydrochloric Acid → 4'-Amino-2'-methyl-biphenyl-3-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

HRID 1678459Notes

Reaction equation

HRID 1678459 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:34])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[CH:15]=2)=[C:10]([CH3:35])[CH:9]=1)(C)(C)C.Cl>CO>[N:28]1([C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:20]([C:16]3[CH:15]=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][C:10]=4[CH3:35])[CH:19]=[CH:18][CH:17]=3)=[O:34])=[CH:27][CH:26]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59822359[2-Methyl-3'-(4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 598223324'-Amino-2'-methyl-biphenyl-3-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[2-Methyl-3′-(4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester (670 mg) was stirred in methanol (15 ml) and 5M HCl (5 ml) at 20 C for 2 days. TLC indicated that the reaction was progressing slowly and so the mixture was heated to reflux for 6 h. The reaction was allowed to cool and was then basified and extracted with dichloromethane. The dried extract was evaporated and the residue purified on silica gel. Elution with dichloromethane:ethanol:0.880 ammonia; 400:8:1 gave a colourless foam which crystallized on standing (354 mg).

Workup

  1. temperatureso the mixture was heated
  2. temperatureto reflux for 6 h
  3. temperatureto cool
  4. extractionextracted with dichloromethane
  5. extractionThe dried extract
  6. customwas evaporated
  7. customthe residue purified on silica gel
  8. washElution with dichloromethane
  9. custom400:8:1 gave a colourless foam which
  10. customcrystallized

Sources & evidence

ORD record
ord-d8a104b8422e4bde876fc137fd52fa05
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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