HCID 11497617, compound → HCID 11706019, compound

HRID 221895Notes

Reaction equation

HRID 221895 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]=[C:23](C)[CH:22]=3)=[CH:16][C:15]=2F)=[O:12])[N:7]([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36](=O)[CH2:37][O:38][CH3:39])=[CH:31][CH:30]=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:29]2[CH:30]=[CH:31][C:32]([NH:35][CH2:36][CH2:37][O:38][CH3:39])=[CH:33][CH:34]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11497617HCID 11497617, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 11706019HCID 11706019, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(3-tert-butyl-5-{[({2-fluoro-4-[(2-methylpyridin-4-yl)oxy]-phenyl}amino)carbonyl]amino}-1H-pyrazol-1-yl)phenyl]-2-methoxyacetamide (500 mg, 0.97 mmol) in anhydrous THF (20 mL) was added borane-methyl sulfide complex (2.0 M solution in THF, 5 mL, 10 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 the organic layer was washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by MPLC (1:1 hexanes/EtOAc) to give 33 mg (7%) of the desired product. 1H-NMR (DMSO-d6) δ 8.65 (s, 1H), 8.42 (d, J=4.8 Hz, 2H), 8.34 (s, 1H), 7.58 (d, J=6.6 Hz, 2H), 7.21 (d, J=6.6 Hz, 2H), 7.06 (d, J=6.9 Hz, 2H), 6.84 (d, J=4.8 Hz, 2H), 6.73 (d, J=6.9 Hz, 2H), 6.43 (s, 1H), 5.23 (s, 1H), 3.57 (t, J=5.7 Hz, 2H), 3.35 to 3.30 (m, 5H), 1.32 (s, 9H); MS LC-MS [M+H]+=529, RT=2.20 min.

Workup

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

Sources & evidence

ORD record
ord-1865fcf2b0b54dfa855dde477566969d
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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