Hydrochloric Acid → HCID 11463807, compound

HRID 2234002Notes

Reaction equation

HRID 2234002 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([O:25]C)=[O:24])=[CH:21][N:22]=2)[CH2:14][CH2:13]1)=[O:10].[OH-].[Li+].O.Cl>C1COCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)[CH2:16][CH2:17]1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68581194HCID 68581194, compound

Product 1

HCID 11463807HCID 11463807, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 320, 250 mg, 0.60 mmol) was dissolved in THF (3 ml). 2 N lithium hydroxide solution in water (3 ml, 6.00 mmol) was added and the mixture was refluxed for 1 hr. The mixture was cooled to room temperature and acidified with 10% HCl solution. The mixture was extracted with EtOAc and organic layer was washed with water twice, dried over sodium sulfate and concentrated to give the desired product. The crude material was dissolved in DMF and purified by semi-preparative reverse phase HPLC eluting with acetonitrile/water (0.1% TFA). The desired fraction were collected and concentrated affording the title compound (28 mg).

Workup

  1. temperaturethe mixture was refluxed for 1 hr
  2. extractionThe mixture was extracted with EtOAc and organic layer
  3. washwas washed with water twice
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-67e1dab7d04541cebf26e49c73849f39
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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