Potassium hydroxy sulfite → HCID 69482744, compound

HRID 2364326Notes

Reaction equation

HRID 2364326 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:27]([NH:29][CH:30]4[CH2:35][CH2:34]S[CH2:32][CH2:31]4)=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.O[O:38][S:39]([O-:41])=O.[K+]>CO.O>[O:38]=[S:39]1(=[O:41])[CH2:34][CH2:35][CH:30]([NH:29][C:27]([C:14]2[C:15](=[O:26])[N:16]([CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[C:17]3[C:12]([C:13]=2[OH:36])=[N:11][CH:10]=[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:18]=3)=[O:28])[CH2:31][CH2:32]1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 69481055HCID 69481055, compound

Product 1

HCID 69482744HCID 69482744, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-(3-pyridinylmethyl)-N-(tetrahydro-2H-thiopyran-4-yl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide (24 mg, 0.05 mmol) in methanol (4 mL) was added Oxone (59.3 mg, 0.10 mmol) as a solution in water (1 mL). The resultant mixture was stirred overnight and then concentrated in vacuo. Ethyl acetate was added followed by water. The organics were washed with brine and the aqueous layer extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by reverse phase preparative HPLC to give the title compound (10 mg, 38%) as a white solid as a format salt. 1H NMR (400 MHz, CDCl3) δ 10.41 (d, J=6.5 Hz, H), 8.58 (s, 1 H), 8.53 (d, J=4.3 Hz, 1 H), 8.41 (s, 1 H), 8.10 (s, 1 H), 7.36 (d, J=8.0 Hz, 1 H), 7.23 (m, 1 H), 7.16 (s, 1 H), 7.01-6.97 (m, 4 H), 5.37 (s, 2 H), 4.26 (m, 1 H), 4.04 (s, 2 H), 3.14 (m, 4 H), 2.49-2.29 (m, 4 H); HRMS m/z calcd for C27H26N4O5FS (M+H)+ 537.1608, found 537.1601.

Workup

  1. concentrationconcentrated in vacuo
  2. additionEthyl acetate was added
  3. washThe organics were washed with brine
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-51931c817442405a9d250d7f74a2940a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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