Water → HCID 10217014, compound

HRID 1792757Notes

Reaction equation

HRID 1792757 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:28]3[C:14](=[CH:15][C:16]4[O:17][CH2:18][CH2:19][CH2:20]S[CH2:22][CH2:23][CH2:24][O:25][C:26]=4[CH:27]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].O[O:30][S:31]([O-:33])=O.[K+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:28]3[C:14](=[CH:15][C:16]4[O:17][CH2:18][CH2:19][CH2:20][S:31](=[O:33])(=[O:30])[CH2:22][CH2:23][CH2:24][O:25][C:26]=4[CH:27]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 962WaterHCID 10151041HCID 10151041, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10217014HCID 10217014, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3-Chloro-4-fluoro-phenyl)-(2,10-dioxa-6-thia-14,16-diaza-tricyclo[9.8.0.013,18]nonadeca-1-(11),12,14,16,18-pentaen-17-yl)-amine (16, 140 mg, 0.33 mmol) was suspended in MeOH, to which was added a cloudy aqueous solution of oxone (monopersulfate compound) (820 mg, 1.33 mmol) at room temperature. The suspension was stirred and monitored by TLC which indicated that the reaction was completed in 4 h. The reaction mixture was poured into H2O (10 mL), and extracted with EtOAc (3×15 mL). The organic layers were collected, dried and concentrated to give a pale yellow residue which was flash chromatographed to give the product as a white solid: 140 mg (93%). 1H NMR (CDCl3) δ 8.75 (s, 1H), 8.00 (d, 1H), 7.24 (s, 1H), 7.26 (s, 1H), 7.42 (s, 1H), 7.30 (d, 1H), 7.25 (s, 1H), 4.40 (t, 4H), 4.75 (t, 2H), 3.40 (t, 2H), 2.55 (m, 2H), 2.23 (m, 2H); ES-MS m/z: 452 (MH+).

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. customThe organic layers were collected
  3. customdried
  4. concentrationconcentrated
  5. customto give a pale yellow residue which
  6. customchromatographed

Sources & evidence

ORD record
ord-3702316ac7f642d386c91c6e27215180
Source dataset
uspto-grants-2006_07
Patent number
US07078409B2

Reaction notes

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