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

HRID 2069063Notes

Reaction equation

HRID 2069063 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:41])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:24][CH:25]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH:33]C(=O)OC(C)(C)C)[CH:28]=3)[CH3:26])=[CH:15][CH:14]=2)[N:7]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:33][C:29]1[CH:28]=[C:27]([CH:25]([CH3:26])[CH2:24][O:23][C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]([NH:12][C:11]([NH:10][C:8]3[N:7]([C:42]4[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=4)[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=3)=[O:41])=[CH:14][CH:15]=2)[CH:32]=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68313493tert-Butyl 4-(1-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

Product 1

HCID 585325561-(4-(2-(2-Aminopyridin-4-yl)propoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the tert-butyl carbamate (56) (0.57 g, 0.88 mmol) in DCM (10.0 mL) was added TFA (5.0 mL) and the resulting dark green solution stirred at RT for 1 hr. The mixture was evaporated in vacuo and the residue was dissolved in MeOH (10.0 mL) and subjected to SCX capture and release to afford the title compound (Intermediate K) as a red oil (488 mg, 98%): m/z 549 (M+H)+ (ES+).

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in MeOH (10.0 mL)

Sources & evidence

ORD record
ord-b87b186e0082495da2d8e6c447e78f4a
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

Loading…