tert-Butanol → HCID 68805055, compound

HRID 2250597Notes

Reaction equation

HRID 2250597 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=3)[N:12]=[C:13]([CH3:22])[C:14]=2[CH2:15][CH2:16][CH2:17][CH2:18]C(O)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].C([N:30]([CH2:33]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1.[C:52]([OH:56])([CH3:55])([CH3:54])[CH3:53]>>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=3)[N:12]=[C:13]([CH3:22])[C:14]=2[CH2:15][CH2:16][CH2:17][CH2:18][NH:30][C:33](=[O:42])[O:56][C:52]([CH3:55])([CH3:54])[CH3:53])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 68802396HCID 68802396, compound

Product 1

HCID 68805055HCID 68805055, compoundYield 23.4%

Procedure

A solution of 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoic acid (100 mg), triethylamine (29.4 mg), and diphenylphosphoryl azide (79.9 mg) in tert-butanol (2 mL) was heated at 80° C. for 8 hours. The cooled reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by p-TLC (hexane-ethyl acetate=3-1) to give tert-butyl 4-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]butylcarbamate (28 mg, 23.4%) as an yellow oil.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by p-TLC (hexane-ethyl acetate=3-1)

Sources & evidence

ORD record
ord-57adbc91114e479cbf496c63250f2bd2
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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