HCID 11497404, compound → HCID 11555353, compound

HRID 1174875Notes

Reaction equation

HRID 1174875 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)=[O:12])[N:7]([C:27]2[CH:39]=[CH:38][C:30]([CH2:31][NH:32][C:33](=O)[CH2:34][O:35][CH3:36])=[CH:29][CH:28]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].B.CSC>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:18][CH:19]=2)=[O:12])[N:7]([C:27]2[CH:39]=[CH:38][C:30]([CH2:31][NH:32][CH2:33][CH2:34][O:35][CH3:36])=[CH:29][CH:28]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11497404HCID 11497404, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 11555353HCID 11555353, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(3-tert-butyl-5-{3-[4-(pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzyl]-2-methoxy-acetamide (200 mg, 0.38 mmol) in anhydrous THF (10 mL) was added borane-methyl sulfide complex (2.0 M solution in THF, 1 mL, 2 mmol), and the reaction was stirred at reflux for 7 h. The reaction mixture was cooled to room temperature, partitioned between EtOAc (50 mL) and water (50 mL), and then the organic layer was separated and washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by MPLC (90:10 CH2Cl2/MeOH) to give 30 mg (15%) of the desired product. 1H-NMR (DMSO-d6) δ 8.79 (s, 1H), 8.42 (d, J=4.8 Hz, 2H), 7.61 to 7.46 (m, 7H), 7.06 (d, J=6.6 Hz, 2H), 6.84 (d, J=4.5 Hz, 2H), 6.44 (s, 1H), 3.85 (s, 2H), 3.49 (t, J=5.7 Hz, 2H), 3.29 (s, 3H), 2.81 (t, J=5.7 Hz, 2H), 1.31 (s, 9H); MS LC-MS [M+H]+=515, RT=2.02 min.

Workup

  1. temperatureat reflux for 7 h
  2. custompartitioned between EtOAc (50 mL) and water (50 mL)
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was purified by MPLC (90:10 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-d5c6b05198df4cdf8d62cf88184a8c1d
Source dataset
uspto-grants-2010_11
Patent number
US07838524B2

Reaction notes

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