tert-Butanol → HCID 69309210, compound

HRID 860475Notes

Reaction equation

HRID 860475 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[N:13][N:12]2[C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=[C:11]2[C:10]=1[C:21]1[CH:22]=[N:23][CH:24]=[C:25]([CH:29]=1)C(O)=O)[CH3:2].C([N:33]([CH2:36]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:45])C=CC=CC=1.[C:55]([OH:59])([CH3:58])([CH3:57])[CH3:56]>>[C:55]([O:59][C:36]([NH:33][C:25]1[CH:29]=[C:21]([C:10]2[C:11]3[N:12]([C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=3)[N:13]=[C:14]([CH3:15])[C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:30])[CH:22]=[N:23][CH:24]=1)=[O:45])([CH3:58])([CH3:57])[CH3:56]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69309306HCID 69309306, compound

Product 1

HCID 69309210HCID 69309210, compound

Procedure

To a solution of 5-[3-(5-ethoxy-5-oxopentyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-4-yl]nicotinic acid (235 mg) and triethylamine (87.1 mg) in t-butanol (10 mL) was added diphenylphosphoryl azide (237 mg) and the mixture was heated under reflux for 2 hours. After evaporation of solvent, the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (20:1–2:1) to give ethyl 5-(4-{5-[(tert-butoxycarbonyl)amino]-3-pyridinyl}-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl)pentanoate as yellow oil (190 mg)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with a mixture of hexane and ethyl acetate (20:1–2:1)

Sources & evidence

ORD record
ord-f860edf7ca7547c3aedc9d82674fb7da
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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