Water ethanol → HCID 57986808, compound

HRID 1516520Notes

Reaction equation

HRID 1516520 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-6dd5ca1fbd6c46d7948ddf6a779957fb
Source dataset
uspto-grants-2012_07
Patent number
US08227495B2

Reaction notes

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