Lithium Hydroxide → HCID 44600485, compound

HRID 1177612Notes

Reaction equation

HRID 1177612 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][N:27]2[CH:31]=[C:30]([C:32]([O:34]CC)=[O:33])[N:29]=[CH:28]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2)[CH2:26][N:27]1[CH:31]=[C:30]([C:32]([OH:34])=[O:33])[N:29]=[CH:28]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67112041HCID 67112041, compound

Product 1

HCID 44600485HCID 44600485, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methyl)-1H-imidazole-4-carboxylate (0.034 g, 0.068 mmol) in THF was added a solution of lithium hydroxide (0.0082 g, 0.34 mmol) in 1.0 mL of water. The reaction mixture was heated to 100° C. for 18 h. The crude reaction mixture was concentrated in vacuo. The residue was diluted with water and the pH was adjusted to 1 with aq. HCl. The solid was collected by filtration, rinsed with water and Et2O, and dried in vacuo at 50° C. for 2 h to afford 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-1H-imidazole-4-carboxylic acid. MS (ESI) m/z: calculated: 470.1; Observed: 471.0 (M++1).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with water
  4. filtrationThe solid was collected by filtration
  5. washrinsed with water and Et2O
  6. customdried in vacuo at 50° C. for 2 h

Sources & evidence

ORD record
ord-c84420ee235246918b1cbee4920205d9
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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