HCID 68323240, compound → HCID 70800909, compound

HRID 1190841Notes

Reaction equation

HRID 1190841 reaction equation
[C:1]1([C:7]2[CH:23]=[CH:22][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][NH2:21])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([O:28][C:29]([N-:31][S:32](N1C=CC(=[N+](C)C)C=C1)(=[O:34])=[O:33])=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[C:1]1([C:7]2[CH:23]=[CH:22][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][NH:21][S:32]([NH:31][C:29](=[O:30])[O:28][C:24]([CH3:26])([CH3:25])[CH3:27])(=[O:33])=[O:34])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 68323240HCID 68323240, compoundHCID 178482962HCID 178482962, compound

Product 1

HCID 70800909HCID 70800909, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-((6-phenylbenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-yl)methanamine (788 mg, 2.44 mmol) (described in WO 2011/074560) in DCM (10 mL) was added N-(tert-butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (737 mg, 2.44 mmol) (Winum, J.-Y. et al., Org. Lett., 3(14):2241-2243 (2001)) and the reaction mixture stirred at rt for 3 days. The mixture was diluted with satd. NH4Cl and extracted with EtOAc (3×). The combined extracts were washed with brine, dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10-100% EtOAc/DCM to give Compound 46a (1.16 g, 95% yield) as a brown oil. LCMS=0.99 min using analytical method (M), 502.0 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.07 (d, J=8.5 Hz, 1H), 8.06 (s, 1H), 7.74 (dd, J=8.4, 1.9 Hz, 1H), 7.68-7.61 (m, 2H), 7.49 (t, J=7.4 Hz, 2H), 7.44-7.36 (m, 1H), 6.96 (br. s., 1H), 5.26 (br. s., 2H), 4.79 (s, 2H), 4.63 (s, 2H), 1.37 (s, 9H).

Workup

  1. additionThe mixture was diluted with satd
  2. extractionNH4Cl and extracted with EtOAc (3×)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 10-100% EtOAc/DCM

Sources & evidence

ORD record
ord-d6ae4b62c19d48e0a98386704f4aee79
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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