Water → 1,1-Dimethylethyl (3-{[5-nitro-4-({4-[(phenylmethyl)oxy]phenyl}amino)-2-pyridinyl]oxy}phenyl)carbamate

HRID 1986380Notes

Reaction equation

HRID 1986380 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[C:19]1[CH:24]=[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:28][CH:27]=2)[C:22]([N+:40]([O-:42])=[O:41])=[CH:21][N:20]=1.O>C1COCC1.CN(C=O)C>[N+:40]([C:22]1[C:23]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:30][CH:31]=2)=[CH:24][C:19]([O:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=2)=[N:20][CH:21]=1)([O-:42])=[O:41]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamateHCID 860451532-Chloro-5-nitro-N-{4-[(phenylmethyl)oxy]phenyl}-4-pyridineamine

Product 1

HCID 866233501,1-Dimethylethyl (3-{[5-nitro-4-({4-[(phenylmethyl)oxy]phenyl}amino)-2-pyridinyl]oxy}phenyl)carbamateYield 92.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 1,1-Dimethylethyl (3-hydroxyphenyl)carbamate (7.05 g, 33.7 mmol) in THF (20 mL) was added dropwise to a suspension of NaH (60% dispersion in oil, 1.34 g, 33.7 mmol) in THF (50 mL). The product of Step 1 (12.0 g, 33.7 mmol) in DMF (100 mL) was then added and the mixture was heated to 60° C. overnight. The reaction mixture was then cooled, poured into H2O and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered and the filtrates were concentrated to give the title compound as a yellow solid (16.4 g, 92%) which was used without purification. MS (ES+) m/e 529 [M+H]+.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrates were concentrated

Sources & evidence

ORD record
ord-e5c19d13f6214901a1d89e66fa9700e1
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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