1,2-Dichloroethane → tert-butyl 4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazine-1-carboxylate

HRID 2173318Notes

Reaction equation

HRID 2173318 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>C(Cl)Cl.O>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12][C:13]([N:26]3[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]3)=[O:15])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 66524945[6-(1H-Tetrazol-1-yl)pyridine-3-yl]acetic acid

Product 1

HCID 67517595tert-butyl 4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid (65 mg, 0.31 mmol), N-Boc-piperazine (88 mg, 0.47 mmol), HOBt (64 mg, 0.47 mmol), EDC (90 mg, 0.47 mmol) and Et3N (96 mg, 0.95 mmol) in DCM (2 mL) was stirred 12 hours at room temperature. Water was added and the mixture was extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by prep-TLC to give tert-butyl 4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazine-1-carboxylate. MS m/z 374 (M+1)+. 1H-NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 8.33 (s, 1H), 7.98˜8.01 (m, 1H), 7.82˜7.85 (m, 1H), 3.73 (s, 2H), 3.56˜3.58 (m, 2H), 3.46˜3.47 (m, 2H), 3.36˜3.39 (m, 4H).

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-617850dcf27447aeab614d09129a7fb3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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