HCID 68323240, compound → HCID 70800909, compound

HRID 1754247Notes

Reaction equation

HRID 1754247 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]>ClCCl.[NH4+].[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

5

Reactant 2

HCID 68323240HCID 68323240, compoundHCID 178482962HCID 178482962, compound

Product 1

HCID 70800909HCID 70800909, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

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 dichloromethane (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 for 3 days. The reaction mixture was diluted with sat′d NH4Cl and the solution extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was purified on silica gel eluting with 10-100% EtOAc/DCM to give Compound 24a (1.2 g, 95% yield) as a brown oil. LCMS=0.99 min using analytical method (B), 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. extractionthe solution extracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on silica gel eluting with 10-100% EtOAc/DCM

Sources & evidence

ORD record
ord-64ae19d5355545039942b198148994bf
Source dataset
uspto-grants-2015_10
Patent number
US09169240B2

Reaction notes

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