Hydrochloric Acid → HCID 58072853, compound

HRID 632909Notes

Reaction equation

HRID 632909 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([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]=[CH:12][N:11]=2)[CH:7]=[CH:6][C:5]=1[F:27].Cl>C1COCC1.O>[NH2:24][C:21]1[N:20]=[CH:19][C:18]([C:17]#[C:16][C:15]2[C:10]([C:8]3[CH:7]=[CH:6][C:5]([F:27])=[C:4]([CH:9]=3)[C:3]([OH:28])=[O:2])=[N:11][CH:12]=[N:13][C:14]=2[CH2:25][CH3:26])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58072559HCID 58072559, compound

Product 1

HCID 58072853HCID 58072853, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The title compound is synthesized according to general procedure GP8 starting from 1.5 g (3.98 mmol) 5-[5-(6-amino-pyridin-3-ylethynyl)-6-ethyl-pyrimidin-4-yl]-2-fluoro-benzoic acid methyl ester using 334 mg (7.97 mmol) LiOH in 20 mL THF and 5 mL water. The reaction mixture is stirred over night at 50° C. Aqueous 1 M HCl is added until pH 5 is reached. The solvent is removed under reduced pressure and the residue is stirred in MeOH. After drying the crude product (0.8 g) is used in the next step without further purification.

Workup

  1. customThe solvent is removed under reduced pressure
  2. stirringthe residue is stirred in MeOH
  3. dry with materialAfter drying the crude product (0.8 g)
  4. customis used in the next step without further purification

Sources & evidence

ORD record
ord-efb8329e6bd74d278eda072eba94c0d8
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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