1,1-Dimethylethyl (2S)-2-[[(6-chloro-3-pyridazinyl)oxy]methyl]-1-azetidinecarboxylate → HCID 21309679, compound

HRID 1416644Notes

Reaction equation

HRID 1416644 reaction equation
C([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=1)(OC(C)(C)C)=O>Cl.C(O)C>[ClH:20].[NH:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 213096631,1-Dimethylethyl (2S)-2-[[(6-chloro-3-pyridazinyl)oxy]methyl]-1-azetidinecarboxylate

Product 1

HCID 21309679HCID 21309679, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A 811 mg sample of 3-(1-BOC-2(S)-azetidinylmethoxy)-6-chloro-pyridazine, prepared as in Example 13a above, was dissolved in 10 mL of satd HCl in ethanol cooled to 0° C., and the reaction was stirred at room temperature for 16 hours. The solvent was removed under vacuum, and the oily residue was dried under high vacuum for 4 hours to provide a solid. The solid was triturated with ether, collected, and recrystallized three times from ethanol/ether to give 118 mg of the title compound. mp 150-151° C. MS (DCI/NH3) m/e: 200 (M+H)+. 1H NMR (DMSO 4,300 MHz) δ: 9.31 (br s, 1H), 7,87 (d, J=9.2 Hz, 1H), 7.44 (d, J=9.2 Hz, 1H), 4.84-4.63 (m, 3H), 3.98-3.83 (m, 2H), 2.59-2.36 (m, 2H). Anal. Calc. for C8H11N3OCI2 : C, 40.70; H, 4.70; N, 17.80; Found C, 40.58; H, 4.59; N, 17.58.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe oily residue was dried under high vacuum for 4 hours
  3. customto provide a solid
  4. customThe solid was triturated with ether
  5. customcollected
  6. customrecrystallized three times from ethanol/ether

Sources & evidence

ORD record
ord-67d4272ae4a94c8a9748c6c42ad64620
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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