Hydrochloric Acid → 5-(4-Aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxylic acid

HRID 883996Notes

Reaction equation

HRID 883996 reaction equation
C1C2C(COC([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[S:30][C:29]([C:31]([O:33]CC)=[O:32])=[CH:28][C:27]=4[NH:36][C:37]4[C:38]5[CH:46]=[CH:45][C:44]([CH:47]([CH3:49])[CH3:48])=[N:43][C:39]=5[N:40]=[CH:41][N:42]=4)=[CH:21][CH:20]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.O.[OH-].[Li+].Cl>O1CCOCC1.O>[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][C:26]2[S:30][C:29]([C:31]([OH:33])=[O:32])=[CH:28][C:27]=2[NH:36][C:37]2[C:38]3[CH:46]=[CH:45][C:44]([CH:47]([CH3:49])[CH3:48])=[N:43][C:39]=3[N:40]=[CH:41][N:42]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67040489Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxylate

Product 1

HCID 670411655-(4-Aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxylic acidYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The product of Example 90E (0.245 g, 0.356 mmol) in 1,4-dioxane (3 mL), was treated with a solution of lithium hydroxide monohydrate (0.0747 g, 1.78 mmol) in water (1.5 mL) at room temperature, the resulting mixture was heated at 60° for 25 minutes. The reaction mixture was cooled, diluted with water (10 mL), adjusted the pH to 3 with 1N aqueous HCl, and the resulting precipitate was collected by vacuum filtration. Washing of the crude product with small volumes of 1,4-dioxane afforded the title compound (0.113 g, 0.258 mmol, 72%). MS (ESI+) m/z 438 (M+H)+, MS (ESI−) m/z 436 (M−H)−.

Workup

  1. temperaturethe resulting mixture was heated at 60° for 25 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting precipitate was collected by vacuum filtration
  4. washWashing of the crude product with small volumes of 1,4-dioxane

Sources & evidence

ORD record
ord-1f3cb0c396174ca0894b7519cffea3d7
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

Loading…