Hydrochloric Acid → HCID 58513382, compound

HRID 1405041Notes

Reaction equation

HRID 1405041 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([C:16]#[C:17][C:18]3[CH:19]=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=3)=[C:14]([CH2:25][CH3:26])[N:13]=[C:12]([NH2:27])[N:11]=2)=[C:6]([F:28])[CH:5]=1.Cl>C1COCC1>[NH2:27][C:12]1[N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[CH:5][C:6]=2[F:28])[C:15]([C:16]#[C:17][C:18]2[CH:19]=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[C:14]([CH2:25][CH3:26])[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67003652HCID 67003652, compound

Product 1

HCID 58513382HCID 58513382, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is synthesized according to general procedure GP8 starting from 200 mg (0.54 mmol) 4-[2-amino-5-(6-amino-pyridin-3-ylethynyl)-6-ethyl-pyrimidin-4-yl]-3-fluoro-benzoic acid methyl ester using 0.81 mL (0.81 mmol) 1 N NaOH in 4 mL THF. After completion of the reaction, the reaction mixture is combined with the mother liquid from the proceeding Suzuki coupling. The pH is adjusted to 4-5 (using 1 N HCl) upon which the product precipitates from the reaction mixture and is isolated by filtration. Yield: 240 mg (58% over two steps).

Workup

  1. customAfter completion of the reaction
  2. customprecipitates from the reaction mixture
  3. customis isolated by filtration

Sources & evidence

ORD record
ord-c49ba9f4c88248208674e4c51b02fdce
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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