Sodium Hydroxide → HCID 67298127, compound

HRID 1520344Notes

Reaction equation

HRID 1520344 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[N:10]=[C:9]2[NH:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=1.[OH-].[Na+]>CN(C=O)C.O>[Cl:30][C:25]1[CH:24]=[C:23]([NH:22][C:9]2[C:8]3[C:13](=[CH:14][CH:15]=[C:6]([CH2:5][CH2:4][C:3]([OH:31])=[O:2])[CH:7]=3)[N:12]=[C:11]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[N:10]=2)[CH:28]=[CH:27][C:26]=1[F:29]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67297938HCID 67297938, compound

Product 1

HCID 67298127HCID 67298127, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[4-(3-chloro-4-fluoro-phenylamino)-2-pyridin-3-yl-quinazolin-6-yl]-propionic acid methyl ester (1.04 g, 2.39 mmol, 1.0 eq.) in DMF (20 mL) was added a solution of NaOH (0.57 g, 14.3 mmol, 6.0 eq.) in H2O (8 mL). The mixture was stirred at room temperature for 2 h. 50 mL of water was added to the mixture. After filtration, the resulting filter cake was washed with water and dried in vacuo to give 933 mg of xxx-a as a yellow solid (yield 93%). LCMS m/z=423.1, 425.1 (M+1) (Method A) (retention time=1.51 min).

Workup

  1. filtrationAfter filtration
  2. filtrationthe resulting filter cake
  3. washwas washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ec429c71ae6640bf980b68357fa0f0dc
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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