4-(1H-1,2,3,4-tetrazol-1-yl)phenol → HCID 57986828, compound

HRID 1869512Notes

Reaction equation

HRID 1869512 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[S:15][CH:16]=[C:17]([CH2:19]Cl)[N:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:21]1([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH:25]=[N:24][N:23]=[N:22]1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[S:15][CH:16]=[C:17]([CH2:19][O:32][C:29]3[CH:30]=[CH:31][C:26]([N:21]4[CH:25]=[N:24][N:23]=[N:22]4)=[CH:27][CH:28]=3)[N:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5429104-(1H-1,2,3,4-tetrazol-1-yl)phenolHCID 57423801HCID 57423801, compound

Product 1

HCID 57986828HCID 57986828, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-Chloromethyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (From Step 1) (300 mg, 0.946 mmol), 4-tetrazol-1-yl-phenol (155 mg, 0.946 mmol), CsCO3 (467 mg, 1.42 mmol) and KI (16 mg, 0.095 mmol) in acetonitrile (10 mL) was heated under reflux for 4 hours. After cooling, the solid was filtered through a pad of celite. The filtrate was concentrated in vacuo. The residue was purified on silica gel (EtOAc-hexanes, 1:1) to afford the desired product. 1H NMR (CDCl3): δ 8.91 (1H, s), 7.63 (2H, d), 7.26 (1H, s), 7.17 (2H, d), 5.24 (2H, s), 4.30 (1H, br), 4.02 (1H, m), 3.20 (1H, m), 3.10 (1H, br), 2.88 (1H, t), 2.21 (1H, m), 1.77 (2H, m), 1.61 (1H, m), 1.47 (9H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered through a pad of celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified on silica gel (EtOAc-hexanes, 1:1)

Sources & evidence

ORD record
ord-fd2967420e004285b5ca83cc8a611239
Source dataset
uspto-grants-2009_12
Patent number
US07638541B2

Reaction notes

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