Acetic Acid → tert-butyl 3-(5-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

HRID 46372Notes

Reaction equation

HRID 46372 reaction equation
[NH:1]([CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)[NH2:2].C(O)(=O)C.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([OH:32])=[C:23]([C:25](=O)/[CH:26]=[CH:27]/N(C)C)[CH:24]=1>C(O)C>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([OH:32])=[C:23]([C:25]2[N:1]([CH:3]3[CH2:4][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6]3)[N:2]=[CH:27][CH:26]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33728788(E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-oneHCID 58042291Tert-butyl 3-hydrazinylazetidine-1-carboxylate

Product 1

HCID 136063615tert-butyl 3-(5-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyl 3-hydrazinoazetidine-1-carboxylate, (Preparation 696, 88.37 g, 0.4247 mol) was dissloved in ethanol (883.7 mL) and the solution was cooled to 0° C. in an ice bath. Acetic acid (97.36 mL, 1.70 mol) was added followed by (2E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, (Preparation 852, 95.86 g, 0.4247 mol) and the resulting slurry was allowed to warm to room temperature then stirred at room temperature for 2 days. The resulting suspension was cooled to 0° C. and the solid was filtered off, washed with cold ethanol (2×40 mL) and dried to give the title compound as a white granular solid, (83.23 g).

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe resulting suspension was cooled to 0° C.
  3. filtrationthe solid was filtered off
  4. washwashed with cold ethanol (2×40 mL)
  5. customdried

Sources & evidence

ORD record
ord-f1a871b908364a589d70f739057d4aa1
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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