Sodium Hydroxide → HCID 68620045, compound

HRID 1162260Notes

Reaction equation

HRID 1162260 reaction equation
[OH-].[Na+].[S:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][C:27]=5[O:29][C@H:30]([CH3:35])[C:31]([O:33]C)=[O:32])[N:22]=[CH:21][N:20]=4)=[CH:15][CH:16]=3)[CH:11]=[N:10]2)[N:5]=[CH:4]1>C1COCC1.CO>[S:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][C:27]=5[O:29][C@H:30]([CH3:35])[C:31]([OH:33])=[O:32])[N:22]=[CH:21][N:20]=4)=[CH:15][CH:16]=3)[CH:11]=[N:10]2)[N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86627841HCID 86627841, compound

Product 1

HCID 68620045HCID 68620045, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide (2N, 1 ml, 2 mmol) was added to a solution of methyl (2R)-2-[(4-{[1-(1,3-thiazol-4-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (480 mg, 1 mmol) in THF (3 ml) and methanol (3 ml). The mixture was stirred at room temperature for 2 hours. After evaporation of the solvents, the pH of the mixture was adjusted to 3 by addition of 2N hydrochloric acid. The precipitate formed was filtered, washed with water and dried under high vacuum to give (2R)-2-[(4-{[1-(1,3-thiazol-4-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoic acid (435 mg, 97%); Mass spectrum MH+ 447.

Workup

  1. customAfter evaporation of the solvents
  2. additionthe pH of the mixture was adjusted to 3 by addition of 2N hydrochloric acid
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-52c0850646d64f9a9abeb183ae71bee0
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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