Sodium Thiosulfate → HCID 178461199, compound

HRID 81224Notes

Reaction equation

HRID 81224 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]3[NH:18][C:17](=[O:19])[O:16][N:15]=3)[CH:11]=[C:10]3[N:20]=[C:21]([CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[F:39])[OH:32])[N:22]([CH2:23][C@H:24]4[CH2:29][CH2:28][C@H:27]([CH3:30])[CH2:26][CH2:25]4)[C:9]=23)[CH:5]=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:22]([CH2:23][C@H:24]4[CH2:29][CH2:28][C@H:27]([CH3:30])[CH2:26][CH2:25]4)[C:21]([C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[F:39])=[O:32])=[N:20][C:10]=3[CH:11]=[C:12]([C:14]3[NH:18][C:17](=[O:19])[O:16][N:15]=3)[N:13]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 178461200HCID 178461200, compound

Product 1

HCID 178461199HCID 178461199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature slurry of 3-{4-(5-chloropyridin-3-yl)-2-[(2-fluorophenyl)(hydroxy)methyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-d]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (Example 7.4 in Table 7, 150 mg, 0.273 mmol) in dichloromethane (4 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (127 mg, 0.301 mmol). The mixture was stirred at room temperature for 1 hour during which time it became a homogeneous solution. Saturated aqueous sodium thiosulfate was added, and the resulting mixture was extracted with ethyl acetate (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification via mass guided reverse phase HPLC (acetonitrile/water+0.1% TFA modifier) afforded 3-{4-(5-chloropyridin-3-yl)-2-[(2-fluorophenyl)carbonyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (TFA salt) as a white solid. MS ESI calcd. for C28H24ClFN6O3 [M+H]+ 547. found 547. 1H NMR (500 MHz, DMSO-d6) δ 13.01 (s, 1H), 8.96 (s, 1H), 8.89 (s, 1H), 8.51 (s, 1H), 8.45 (s, 1H), 7.85-7.87 (m, 2H), 7.45-7.41 (m, 2H), 4.25 (d, J=6.5 Hz, 2H), 1.43-1.40 (m, 2H), 1.15-1.02 (m, 2H), 0.86-0.80 (m, 2H), 0.73-0.65 (m, 5H), 0.55-0.50 (m, 2H).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (2×)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via mass

Sources & evidence

ORD record
ord-7e43d8335bf1436e930622a39f811a0a
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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