Water → Isopropyl 4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidine-1-carboxylate

HRID 1928601Notes

Reaction equation

HRID 1928601 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[N:11]=[C:10]([CH2:12][O:13][C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH:24]=[N:23][N:22]=[N:21]4)=[N:18][CH:19]=3)[CH:9]=[N:8]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34].O>C(OCC)(=O)C>[N:20]1([C:17]2[N:18]=[CH:19][C:14]([O:13][CH2:12][C:10]3[CH:9]=[N:8][N:7]([CH:4]4[CH2:3][CH2:2][N:1]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:6][CH2:5]4)[N:11]=3)=[CH:15][CH:16]=2)[CH:24]=[N:23][N:22]=[N:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 577083955-((2-(piperidin-4-yl)-2H-1,2,3-triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine2×

Product 1

HCID 25176686Isopropyl 4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-((2-(piperidin-4-yl)-2H-1,2,3-triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine (Intermediate 15) (0.300 g, 0.917 mmol) in ethyl acetate (3 mL) was added triethylamine (0.169 mL, 1.22 mmol) and isopropyl chloroformate (1.10 mL, 1M solution in toluene, 1.10 mmol). The resulting solution was stirred for 1 hour. Water was added and the solution was extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (1:1 hexanes/ethyl acetate) to obtain the expected product. 1H NMR (CDCl3): δ 9.45 (1H, s), 8.28 (1H, d), 8.03 (1H, d), 7.71 (1H, s), 7.58 (1H, dd), 5.28 (2H, s), 4.95 (1H, m), 4.64 (1H, m), 4.22 (1H, m), 2.21 (2H, m), 2.14 (2H, m), 1.26 (6H, d).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-8791bd8258be425098256f6604d71841
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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