Lithium Hydroxide → HCID 18378997, compound

HRID 2298976Notes

Reaction equation

HRID 2298976 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[NH:14][C:15]3[C:16]([N:21]=2)=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>>[NH:14]1[C:15]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[N:21]=[C:13]1[CH2:12][CH:9]1[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 18340693HCID 18340693, compound

Product 1

HCID 18378997HCID 18378997, compound

Conditions

Temperature
65 °C

Procedure

The cis/trans mixture of 4-(1H-imidazo[4,5-b]pyridin-2-ylmethyl)-cyclohexanecarboxylic acid ethyl ester (Compound AAA) (1 g) was dissolved in a minimal amount of TBF (10 mL) and mixed with concentrated aqueous LiOH (5 mL). The resulting reaction mixture was stirred vigorously and heated at 65° C. for 3 h. After cooling and concentration, the reaction was acidified to pH 4 with dilute HCl and concentrated to dryness: mass spectrum m/z 260 [(M+H)+; calcd for C14H 18N3O2: 259].

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling
  3. concentrationconcentration
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d50e104de73d418e9c8dd7b229e7efd3
Source dataset
uspto-grants-2002_12
Patent number
US06495561B2

Reaction notes

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