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Dichloromethane → N-tert-butyl-4-[3-{3-[(diphenylmethylidene)amino]phenyl}-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridin-2-amine

HRID 45837
Notes
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Reaction equation

HRID 45837 reaction equation
[C:1]1([C:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[C:19]([C:20]4[CH:25]=[CH:24][N+:23]([O-])=[CH:22][CH:21]=4)=[CH:18][N:17]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[N:16]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:42]([NH2:46])([CH3:45])([CH3:44])[CH3:43].C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.ClCCl>FC(C1C=CC=CC=1)(F)F>[C:42]([NH:46][C:24]1[CH:25]=[C:20]([C:19]2[C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([N:8]=[C:7]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:10]=3)=[N:16][N:17]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH:18]=2)[CH:21]=[CH:22][N:23]=1)([CH3:45])([CH3:44])[CH3:43]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 86654335N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-(1-oxidopyridin-4-yl)-1H-pyrazol-3-yl]aniline

Product 1

HCID 86654336N-tert-butyl-4-[3-{3-[(diphenylmethylidene)amino]phenyl}-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridin-2-amine
Yield 73%

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

200 mg (0.4 mmol) of N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-(1-oxidopyridin-4-yl)-1H-pyrazol-3-yl]aniline were suspended in 50 ml of trifluoromethylbenzene and 210 μl (2 mmol) of tert-butylamine were added under stirring at room temperature. The mixture was cooled to 0° C. and 260 mg (0.8 mmol) of p-toluensulfonic anhydride were added. The reaction was maintained in the same conditions for 2.5 hours. Then the same amounts of reactants and 2 ml of dichloromethane to obtain a clear solution were added and after further 2 hours the reaction went to completion. The solvent was evaporated and the residue taken up in dichloromethane and washed with water. The organic phase was dried over Na2SO4 and evaporated to dryness, giving 161 mg (73% yield) of the title compound.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. temperatureThe reaction was maintained in the same conditions for 2.5 hours
  3. additionwere added and after further 2 hours the reaction
  4. customThe solvent was evaporated
  5. washwashed with water
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-419a6d40644b4cc2890be3f1b934b1ae
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541575B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes