Sodium Hydroxide → HCID 28875795, compound

HRID 1170875Notes

Reaction equation

HRID 1170875 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]2=[N:8][C:7]=1[N:15]([C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH3:16])=[O:5])C.C[O:27][C:28]([C:30]1[N:34]2[CH2:35][CH2:36][CH2:37][CH2:38][C:33]2=[N:32][C:31]=1N(C(=O)C1C=CC=C(Cl)C=1)C)=[O:29].[OH-].[Na+]>CO.O1CCOCC1.O>[Cl:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([N:15]([CH3:16])[C:7]1[N:8]=[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]2[C:6]=1[C:4]([OH:5])=[O:3])=[O:25].[N:32]1[CH:31]=[C:30]([C:28]([OH:29])=[O:27])[N:34]2[CH2:35][CH2:36][CH2:37][CH2:38][C:33]=12

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 57465134HCID 57465134, compoundHCID 57465135HCID 57465135, compound

Product 2

HCID 28875795HCID 28875795, compoundHCID 57465089HCID 57465089, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21966525Dioxane MethanolSolvent

Procedure

2-[(3-chloro-benzoyl)-methyl-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester and 2-[(3-chloro-benzoyl)-methyl-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid methyl ester (1.0 mmol together) were dissolved in a solution of 16 mL MeOH/dioxan/4 M NaOH in water in a ratio of 15/4/1, and the solution was stirred over night at room temperature. Further NaOH in water (1.5 mL, 6 mmol) was added thereto. After 45 minutes the solvent was removed under vacuum, EtOAc (60 mL) was added thereto and the organic phase was washed with 0.5 M KHSO4 in water (50 mL). The aqueous phase was extracted with EtOAc (60 mL), the combined organic phases were washed with saturated aqueous NaCl solution (80 mL) and dried over sodium sulphate, and the solvent was removed under vacuum. 234 g (70% over two stages) of the desired product 2-(3-chloro-benzoyl)-methyl-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid were obtained.

Workup

  1. customAfter 45 minutes the solvent was removed under vacuum, EtOAc (60 mL)
  2. additionwas added
  3. washthe organic phase was washed with 0.5 M KHSO4 in water (50 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (60 mL)
  5. washthe combined organic phases were washed with saturated aqueous NaCl solution (80 mL)
  6. dry with materialdried over sodium sulphate
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-288b7229d5ff48f6997a0a2e1134497e
Source dataset
uspto-grants-2010_11
Patent number
US07829568B2

Reaction notes

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