Water ethanol → HCID 57986808, compound

HRID 871939Notes

Reaction equation

HRID 871939 reaction equation
[N:1]1([C:6]2[CH:26]=[CH:25][C:9]([O:10][CH2:11][C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]#[N:24])[CH2:19][CH2:18]4)[S:15][CH:16]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.C([OH:29])C.O>Cl>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([NH2:24])=[O:29])[CH2:19][CH2:18]4)[S:15][CH:16]=3)=[CH:25][CH:26]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 19096565Water ethanolHCID 57986843HCID 57986843, compound

Product 1

HCID 57986808HCID 57986808, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-[4-(4-Tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidine-1-carbonitrile (1.07 g, 2.92 mmol) was dissolved in 4 N HCl in ethanol/water (1:1). The solution was refluxed for 1 hour, cooled and the solid precipitate was filtered off. The filtrate was neutralized by the addition of excess sodium carbonate. The excess sodium carbonate was filtered off and the filtrate was diluted with EtOAc. The solution was washed with water, separated, dried (Na2SO4), filtered and concentrated. The residual oil was chromatographed on silica gel (1:1 Hexanes/EtOAc) to afford the desired compound. 1H NMR (CDCl3): δ 8.92 (1H, s), 7.60 (2H, d), 7.23 (1H, s), 7.167 (2H, d), 5.21 (2H, s), 4.25 (2H, m), 4.15 (2H, m), 3.22 (1H, m), 2.90 (2H, m), 2.18 (2H, m).

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. temperaturecooled
  3. filtrationthe solid precipitate was filtered off
  4. additionThe filtrate was neutralized by the addition of excess sodium carbonate
  5. filtrationThe excess sodium carbonate was filtered off
  6. additionthe filtrate was diluted with EtOAc
  7. washThe solution was washed with water
  8. customseparated
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residual oil was chromatographed on silica gel (1:1 Hexanes/EtOAc)

Sources & evidence

ORD record
ord-791b7ce410b84f4782c0c0b28871c172
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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