Lithium Hydroxide → 2-{4-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazin-1-yl}-propionic acid

HRID 2359583Notes

Reaction equation

HRID 2359583 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[N:14][C:15]([NH:18][C:19]3[N:20]=[CH:21][C:22]4[CH:27]=[C:26]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[N:25]([CH:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[C:23]=4[N:24]=3)=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)[CH3:5].[Li+].[OH-]>C1COCC1.O>[CH:33]1([N:25]2[C:23]3[N:24]=[C:19]([NH:18][C:15]4[N:14]=[CH:13][C:12]([N:9]5[CH2:8][CH2:7][N:6]([CH:4]([CH3:5])[C:3]([OH:38])=[O:2])[CH2:11][CH2:10]5)=[CH:17][CH:16]=4)[N:20]=[CH:21][C:22]=3[CH:27]=[C:26]2[C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58315412HCID 58315412, compound

Product 1

HCID 448200192-{4-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazin-1-yl}-propionic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{4-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazin-1-yl}-propionic acid methyl ester (250 mg, 0.48 mmol) in 10 mL of THF is added a solution of LiOH (19 mg, 48 mmol) in 10 mL of H2O. After 18 h stirring at room temperature, the resulting mixture is concentrated and diluted with H2O and adjusted to pH=6 with 1 N HCl. Ished with dichloromethane then solids precipitated and collected to give 2-{4-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazin-1-yl}-propionic acid (225 mg, 94%). MS (ESI) m/z 507.3 (M+H)+

Workup

  1. concentrationthe resulting mixture is concentrated
  2. additiondiluted with H2O
  3. customsolids precipitated
  4. customcollected

Sources & evidence

ORD record
ord-41d4c3ac716d4389a7c4fae200d4e5dd
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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