1-Isopropylhydrazine hydrochloride → {2-[4-[1,3]Dioxolan-2-ylmethyl-5-(4-fluoro-phenyl)-1-isopropyl-1H-pyrazol-3-yl]-ethyl}-carbamic acid benzyl ester

HRID 606621Notes

Reaction equation

HRID 606621 reaction equation
Cl.[CH:2]([NH:5][NH2:6])([CH3:4])[CH3:3].[CH2:7]([O:14][C:15](=[O:21])[NH:16][CH2:17][CH2:18][CH:19]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]=[C:30]([N+]([O-])=O)[CH2:31][CH:32]2[O:36][CH2:35][CH2:34][O:33]2)=[CH:25][CH:24]=1>CCN(CC)CC>[CH2:7]([O:14][C:15](=[O:21])[NH:16][CH2:17][CH2:18][C:19]1[C:30]([CH2:31][CH:32]2[O:36][CH2:35][CH2:34][O:33]2)=[C:29]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[N:5]([CH:2]([CH3:4])[CH3:3])[N:6]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 855731-Isopropylhydrazine hydrochlorideHCID 10398106Benzyl (3-Oxopropyl)carbamateHCID 67047481HCID 67047481, compound

Product 1

HCID 54754013{2-[4-[1,3]Dioxolan-2-ylmethyl-5-(4-fluoro-phenyl)-1-isopropyl-1H-pyrazol-3-yl]-ethyl}-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of isopropylhydrazine hydrochloride (1.07 g, 9.7 mmol) and (3-oxo-propyl)-carbamic acid benzyl ester (2.0 g, 9.7 mmol) in Et3N (20 mL) was heated at 60° C. After 1 h, 2-[3-(4-fluoro-phenyl)-2-nitro-allyl]-[1,3]dioxolane (2.2 g, 8.7 mmol) was added. After 16 h at 60° C., the mixture was cooled to rt and concentrated. The residue was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), and concentrated. Purification by FCC gave the title compound.

Workup

  1. waitAfter 16 h at 60° C.
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by FCC

Sources & evidence

ORD record
ord-6649126592ae4aaabd70aa54307bddf2
Source dataset
uspto-grants-2011_03
Patent number
US07915404B2

Reaction notes

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