Trifluoroacetic acid → 1-(4-(2-(2-aminopyridin-4-yl)ethoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea

HRID 2069030Notes

Reaction equation

HRID 2069030 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][O:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([NH:27][C:28]([NH:30][C:31]3[N:35]([C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=4)[N:34]=[C:33]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:32]=3)=[O:29])=[CH:19][CH:18]=2)[CH:11]=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][O:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([NH:27][C:28]([NH:30][C:31]3[N:35]([C:36]4[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=4)[N:34]=[C:33]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:32]=3)=[O:29])=[CH:19][CH:18]=2)[CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58416761tert-butyl-4-(2-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido) naphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate

Product 1

HCID 584167451-(4-(2-(2-aminopyridin-4-yl)ethoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the carbamate (23) (1.35 g, 2.20 mmol) in DCM (10 mL) was added TFA (10 mL). After stirring at RT for 2 hr, the volatiles were evaporated and the residue was taken up in EtOAc (50 mL) and extracted with saturated aq NaHCO3 solution (50 mL). The organic layer was separated and was washed with brine (50 mL), and then dried and evaporated to give the title compound (Intermediate D) as a pale pink solid (1.20 g, 100%): m/z 535 (M+H)+ (ES+).

Workup

  1. customthe volatiles were evaporated
  2. extractionextracted with saturated aq NaHCO3 solution (50 mL)
  3. customThe organic layer was separated
  4. washwas washed with brine (50 mL)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-fcda9685b2cf40dc9daa4db68e9fb910
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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