1-(5-t-Butyl-2-{3-[5-(4-methoxy-benzyl)-(R)-3-methyl-1,1,4-trioxo-1lambda6-[1,2,5]-thiadiazolidin-2-ylmethyl]-phenyl}-2H-pyrazol-3-yl)-3-naphthalen-1-yl-urea → HCID 58842919, compound

HRID 16970Notes

Reaction equation

HRID 16970 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:35][C:36]([NH:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH:42]=[CH:41][CH:40]=2)=[O:37])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]3[C@H:21]([CH3:22])[C:20](=[O:23])[N:19](CC4C=CC(OC)=CC=4)[S:18]3(=[O:34])=[O:33])[CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:35][C:36]([NH:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH:42]=[CH:41][CH:40]=2)=[O:37])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]3[C@H:21]([CH3:22])[C:20](=[O:23])[NH:19][S:18]3(=[O:34])=[O:33])[CH:11]=2)[N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 866023101-(5-t-Butyl-2-{3-[5-(4-methoxy-benzyl)-(R)-3-methyl-1,1,4-trioxo-1lambda6-[1,2,5]-thiadiazolidin-2-ylmethyl]-phenyl}-2H-pyrazol-3-yl)-3-naphthalen-1-yl-urea

Product 1

HCID 58842919HCID 58842919, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(5-t-Butyl-2-{3-[5-(4-methoxy-benzyl)-(R)-3-methyl-1,1,4-trioxo-1λ6-[1,2,5]-thiadiazolidin-2-ylmethyl]-phenyl}-2H-pyrazol-3-yl)-3-naphthalen-1-yl-urea (20 mg, 0.030 mmol) in trifluoroacetic acid (2 mL) was stirred at 50° C. for 4 h. After the solvent was removed, the residue was purified by preparative-HPLC to afford 1-{5-t-butyl-2-[3-((R)-3-methyl-1,1,4-trioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-phenyl]-2H-pyrazol-3-yl}-3-naphthalen-1-yl-urea as a white powder (6 mg). 1H NMR (DMSO-d6): 8.99 (s, 1H), 8.80 (s, 1H), 8.00 (d, J=7.2 Hz, 1H), 7.90 (d, J=7.2 Hz, 2H), 7.60-7.64 (m, 2H), 7.44-7.54 (m, 7H), 6.41 (s, 1H), 4.31-4.49 (dd, J=8.0 Hz, 2H), 4.03 (q, J=7.6 Hz, 1H), 1.27 (s, 9H), 1.19 (d, J=8.0 Hz, 3H). MS (ESI) m/z: 533 (M+H+).

Workup

  1. customAfter the solvent was removed
  2. customthe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-54b657c463cf4970820e6080af5b66c5
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Reaction notes

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