Sodium Thiosulfate → HCID 58902358, compound

HRID 1640188Notes

Reaction equation

HRID 1640188 reaction equation
[CH3:1][CH:2]1[NH:6][C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][C:18]([C:24]([NH:26][C:27]3[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([O:37][CH2:38][CH2:39][N:40]5[CH2:44][CH2:43][CH2:42][CH2:41]5)[CH:28]=3)=[O:25])=[CH:17]4)[CH:10]=[CH:9][N:8]=2)=[N:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][C:18]([C:24]([NH:26][C:27]3[CH:32]=[C:31]([C:33]([F:34])([F:36])[F:35])[CH:30]=[C:29]([O:37][CH2:38][CH2:39][N:40]5[CH2:41][CH2:42][CH2:43][CH2:44]5)[CH:28]=3)=[O:25])=[CH:17]4)[CH:10]=[CH:9][N:8]=2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2×HCID 516892Sodium BicarbonateHCID 58902450HCID 58902450, compound

Product 1

HCID 58902358HCID 58902358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-{[2-(5-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-4-yl]oxy}-N-[3-(2-pyrrolidin-1-ylethoxy)-5-(trifluoromethyl)phenyl]quinoline-3-carboxamide I-218 (0.500 g, 0.83 mmol) in DCM (20 mL) at 0° C. was added Dess-Martin periodinane (0.701 g, 1.65 mmol). The reaction mixture was allowed to stir at 0° C. overnight. Additional Dess-Martin periodinane (0.140 g, 0.32 mmol) was added and the reaction mixture was allowed to warm to rt until reaction was complete. Aq Na2S2O3 was added and the reaction mixture was allowed to stir at rt for 10 min before the addition of sat. aq. NaHCO3. The reaction mixture was extracted with DCM, concentrated, and purified by column chromatography to give 6-{[2-(5-methyl-1H-imidazol-2-yl)pyridin-4-yl]oxy}-N-[3-(2-pyrrolidin-1-ylethoxy)-5-(trifluoromethyl)phenyl]-quinoline-3-carboxamide I-409. 1H NMR (300 MHz, d6-DMSO, HCl salt) δ: 11.21 (s, 1H), 10.67-10.85 (br s, 1H), 9.45 (s, 1H), 9.11 (s, 1H), 8.71 (d, 1H), 8.29 (d, 1H), 8.13 (m, 1H), 8.04 (m, 1H), 7.94-7.91 (br s, 2H), 7.88-7.82 (m, 1H), 4.49-4.40 (m, 2H), 3.67-3.55 (m, 5H), 3.18-3.05 (m, 3H), 2.32 (s, 3H), and 2.08-1.84 (m, 5H). LCMS: (FA) ES+ 603.2, ES− 600.8.

Workup

  1. temperatureto warm to rt until reaction
  2. extractionThe reaction mixture was extracted with DCM
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-cae02ca49c0f40838e3d4dcba99c54fb
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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