Lithium hydroxide, monohydrate → HCID 59380363, compound

HRID 2353834Notes

Reaction equation

HRID 2353834 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[CH:35]=[CH:34][C:9]2[C:10]3[C:15]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=5)=[C:19]([Cl:32])[CH:18]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:33][C:8]=2[CH:7]=1)C.O.[OH-].[Li+]>C1COCC1.O>[Cl:32][C:19]1[CH:18]=[C:17]([NH:16][C:15]2[C:10]3[C:9]4[CH:34]=[CH:35][C:6]([CH2:5][C:4]([OH:36])=[O:3])=[CH:7][C:8]=4[S:33][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59380413HCID 59380413, compound

Product 1

HCID 59380363HCID 59380363, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of {4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl}-acetic acid ethyl ester (400 mg, 0.766 mmol) in THF (10 mL) was added a solution of lithium hydroxide monohydrate (161 mg, 3.83 mmol) in water (3 mL), and the resulting mixture was stirred at rt overnight. The solvent was evaporated, and aq. NaOH (0.2 N, 5 mL) was added to the residue, and the mixture was washed with diethyl ether (2×8 mL). The pH of the aqueous layer was adjusted to 5 by addition of 0.5 N HCl, and it was then extracted with EtOAc (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated to give the product as a slightly brown solid. (350 mg, 93%). LCMS RT=3.66 min, [M+H]+=494.1.

Workup

  1. customThe solvent was evaporated
  2. additionaq. NaOH (0.2 N, 5 mL) was added to the residue
  3. washthe mixture was washed with diethyl ether (2×8 mL)
  4. additionThe pH of the aqueous layer was adjusted to 5 by addition of 0.5 N HCl, and it
  5. extractionwas then extracted with EtOAc (3×25 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give the product as a slightly brown solid

Sources & evidence

ORD record
ord-c65f0a4f85af478aa337d2ca42daa7b9
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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