Hydrochloric Acid → HCID 67354845, compound

HRID 1850596Notes

Reaction equation

HRID 1850596 reaction equation
C1COCC1.C[O:7][C:8](=[O:36])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:17]=[CH:18][C:19]3[CH:24]=[C:23]([C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[N:22]([CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[C:20]=3[N:21]=2)=[N:11][CH:10]=1.[Li+].[OH-].Cl>CO.O>[CH:30]1([N:22]2[C:20]3[N:21]=[C:16]([NH:15][C:12]4[CH:13]=[CH:14][C:9]([C:8]([OH:36])=[O:7])=[CH:10][N:11]=4)[N:17]=[CH:18][C:19]=3[CH:24]=[C:23]2[C:25](=[O:29])[N:26]([CH3:27])[CH3:28])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67354499HCID 67354499, compound

Product 1

HCID 67354845HCID 67354845, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a 25 mL solution of THF, water and MeOH (2:2:1) containing 6-(7-cyclohexyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid methyl ester (860 mg, 2.04 mmol) was added solid LiOH (244 mg, 10.2 mmol). After stirring at 50° C. for 90 m, reaction was acidified to pH 6 with 1M HCl and then partitioned into two phases with a mixture of water, isopropyl alcohol and chloroform. The organic layer was removed and concentrated to yield 6-(7-cyclohexyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid (805 mg, 1.97 mmol) in 97% yield. MS m/z 409.6 (M÷H)+

Workup

  1. custompartitioned into two phases with a mixture of water, isopropyl alcohol and chloroform
  2. customThe organic layer was removed
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e5d47d85a9e242fd8559693b1aae23ba
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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