tert-Butanol → HCID 21101591, compound

HRID 1353329Notes

Reaction equation

HRID 1353329 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[O:22])[CH2:17][CH2:16]3)=[CH:7][C:8](C(O)=O)=[N:9]2)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1.C([N:50]([CH2:53]C)CC)C.[C:55]([OH:59])([CH3:58])([CH3:57])[CH3:56]>>[C:55]([O:59][C:53]([NH:50][C:8]1[CH:7]=[C:6]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[O:22])[CH2:17][CH2:16]2)[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)=[O:38])([CH3:58])([CH3:57])[CH3:56]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 21101788HCID 21101788, compound

Product 1

HCID 21101591HCID 21101591, compound

Procedure

A solution of 7-chloro-4-[4-(4-fluorophenylaminocarbonyl)piperazin-1-yl]quinoline-2-carboxylic acid (215 mg, 0.5 mmol), diphenylphosphoryl azide (DPPA, 144 μL, 0.65 mmol), and triethylamine (92 μL, 0.65 mmol) in t-butanol (5 mL) is heated at 105° C. in an Ar atmosphere for 3 h. The solvent is removed, and the residue is dissolved in EtOAc, washed with water, dried (MgSO4), and concentrated. Purification by column chromatography with CH2Cl2-MeOH affords the title product.

Workup

  1. customThe solvent is removed
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by column chromatography with CH2Cl2-MeOH

Sources & evidence

ORD record
ord-00147eaa66f440f1bc22bf6df89091dc
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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