Tetrahydrofuran → HCID 70979845, compound

HRID 1749075Notes

Reaction equation

HRID 1749075 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([CH:9]([C:11](=[O:29])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C1C[O:34][CH2:33]C1>>[C:1]([O:5][C:6](=[O:30])[N:7]([CH:9]([C:11](=[O:29])[NH:12][C:13]1[N:14]=[C:15]2[N:20]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[C:33](=[O:34])[NH:19][C:16]2=[CH:17][CH:18]=1)[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 71003382HCID 71003382, compound

Product 1

HCID 70979845HCID 70979845, compound

Conditions

Temperature
70 °C

Procedure

A solution of the product from Step 3, in THF (3 mL), was added to a solution of N,N′-carbonyldiimidazole (110 mg, 0.68 mmol) in THF (3 mL). The mixture was then heated at 70° C. for 3 hours. After allowing to cool, the mixture was concentrated in vacuo, treated with water and then left overnight. The product was extracted with EtOAc. The EtOAc layer was washed successively with aqueous potassium hydrogensulfate solution, brine and then dried (MgSO4). The solution was concentrated to ˜1 mL and then Et2O (3 mL) was added. The resulting precipitate was collected by filtration to give {1-[3-(4-chloro-benzyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-ylcarbamoyl]ethyl}-methyl-carbamic acid tert-butyl ester (90 mg) as a white crystalline solid. MS: [M+H]+=460.

Workup

  1. temperatureto cool
  2. concentrationthe mixture was concentrated in vacuo
  3. additiontreated with water
  4. extractionThe product was extracted with EtOAc
  5. washThe EtOAc layer was washed successively with aqueous potassium hydrogensulfate solution, brine
  6. dry with materialdried (MgSO4)
  7. concentrationThe solution was concentrated to ˜1 mL
  8. additionEt2O (3 mL) was added
  9. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-055795e5fed44fb191ca177394f52d53
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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