Toluene → HCID 10644860, compound

HRID 1839455Notes

Reaction equation

HRID 1839455 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13](=[O:20])[C:14]3[S:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26].C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(C)C=CC=CC=1.[NH4+].[Cl-]>C(OCC)(=O)C.C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:16][C:15]2[CH:17]=[CH:18][S:19][C:14]=2[C:13]([NH:21][C:22]2[CH:29]=[CH:28][CH:27]=[C:24]([C:25]#[N:26])[CH:23]=2)=[O:20])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 1140TolueneHCID 167023-AminobenzonitrileHCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10684544HCID 10684544, compound

Product 1

HCID 10644860HCID 10644860, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(4-t-butylphenyl)-4H-thieno[3,2-d]-[1,3]oxazin-4-one (400 mg, 1.4 mmol), 3-aminobenzonitrile (165 mg, 1.4 mmol) and THF (5 mL) was added 0.5 M potassium hexamethyldisilazide in toluene (3.08 mL, 1.54 mmol) and stirred for 15 min. The reaction was added NH4Cl and ethyl acetate. The organic layer was washed with water (3×) and brine, MgSO4 dried and concentrated. The residue was chromatographed (20% THF/hexanes) to give the title compound as a solid (580 mg, 51%); 1.37 (s, 9H), 7.47 (m, 4H), 7.57 (d, 2H, J=8.4 HZ); 7.68 (m, 1H), 7.98 (d, 2H, J=8.4 Hz); 8.20 (s, 1H); 8.42 (d, 1H, J=5.7 Hz); 11.80 (s, 1H); MS(FD): 403.

Workup

  1. washThe organic layer was washed with water (3×) and brine, MgSO4
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed (20% THF/hexanes)

Sources & evidence

ORD record
ord-9e737a2e6be942d39ae6b8d9b7f5b750
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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