Methyl iodide → HCID 11200879, compound

HRID 899221Notes

Reaction equation

HRID 899221 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[NH:18][C:17](=[O:19])[O:16][C:15]([CH2:25][CH3:26])([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)[C:14]=3[CH:27]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:28]C(C)([O-])C.[K+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[N:18]([CH3:28])[C:17](=[O:19])[O:16][C:15]([CH2:25][CH3:26])([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)[C:14]=3[CH:27]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11153898HCID 11153898, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11200879HCID 11200879, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-[(3-chloro-4-fluorophenyl)amino]-4-ethyl-4-thien-2-yl-1,4-dihydro-2H-3,1-benzoxazin-2-one (0.16 g, 0.39 mmol) in DMF (4 mL) was added potassium t-butoxide (0.05 g, 0.42 mmol) at room temperature. After 10 minutes, methyl iodide (0.05 mL, 0.80 mmol) was added. After 45 minutes, the reaction solution was quenched with ammonium chloride solution (sat) and extracted with ethyl acetate. The organic layer washed several times with brine and dried over magnesium sulfate. The solvent was removed to give 6-[(3-chloro-4-fluorophenyl)amino]-4-ethyl-1-methyl-4-thien-2-yl-1,4-dihydro-2H-3,1-benzoxazin-2-one as a red solid (0.12 g, 73%). 1H NMR (DMSO-d6): δ 8.31 (s, 1H), 7.53 (m, 1H), 7.27 (t, J=9.1 Hz, 1H), 7.16 (d, J=8.7 Hz, 1H), 7.10 (d, J=8.6 Hz, 1H), 7.05 (m, 1H), 7.0 (m, 2H), 6.93 (m, 2H), 3.24 (s, 3H), 2.43 (m, 2H), 0.96 (t, J=5.9 Hz, 3H); MS (ESI) m/z 417/419 ([M+H]+); MS (ESI) m/z 415/417 ([M−H]−); Anal. calcd for C21H18ClFN2O2S: C, 60.50; H, 4.35; N, 6.72. Found: C, 60.22; H, 4.34; N, 6.63.

Workup

  1. waitAfter 45 minutes
  2. customthe reaction solution was quenched with ammonium chloride solution (sat)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer washed several times with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-d1622ea732d345dbbacaef55e551a023
Source dataset
uspto-grants-2008_04
Patent number
US07354915B2

Reaction notes

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