HCID 57394325, compound → HCID 57396083, compound

HRID 388105Notes

Reaction equation

HRID 388105 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=4)[N:15]=3)[NH:10][C:9]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(CN2C3C(=N[CH:39]=[C:40]([C:43]4C=CC(C(OC)=O)=CC=4)[N:41]=3)NC2=O)CCCCC1>[OH-].[Li+].O1CCCC1>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:18]=[CH:19][C:20]([C:21]([NH:41][CH:40]([CH3:43])[CH3:39])=[O:22])=[CH:24][CH:25]=4)[N:15]=3)[NH:10][C:9]2=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 57394325HCID 57394325, compoundHCID 57403086HCID 57403086, compound

Product 1

HCID 57396083HCID 57396083, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(3-(Cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzoic acid. A solution of methyl 4-(3-(cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzoate (See Example 56.A) (350 mg, 0.95 mmol) in 1N lithium hydroxide (4.5 mL) and tetrahydrofuran (4.5 mL) was allowed to stir at rt for 19 h. Upon completion of the reaction, the volatiles were removed under reduced pressure. The residue was treated with 1N hydrochloric acid and sonicated. The resulting precipitate was collected by vacuum filtration, and dried under high vacuum to afford the title compound (300 mg, 90% yield) as a tan solid. MS (ESI) m/z 353.3 [M+1]+.

Workup

  1. customUpon completion of the reaction
  2. customthe volatiles were removed under reduced pressure
  3. additionThe residue was treated with 1N hydrochloric acid
  4. customsonicated
  5. filtrationThe resulting precipitate was collected by vacuum filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-4207a270bc8b4dcca0e55c41e866f1ba
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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