Hydrochloric Acid → HCID 60198483, compound

HRID 1850055Notes

Reaction equation

HRID 1850055 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]C(=O)OC(C)(C)C)=[C:5]([NH:17][C:18](=[O:27])/[CH:19]=[CH:20]/[C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)[CH:4]=1>O1CCOCC1.C(OCC)C>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([F:2])=[CH:4][C:5]=1[NH:17][C:18](=[O:27])/[CH:19]=[CH:20]/[C:21]1[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86702816HCID 86702816, compound

Product 1

HCID 60198483HCID 60198483, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Protecting group removal was effected by addition of a 4M solution of HCl in dioxane (2.5 mL) to a solution of (E)-tert-butyl (4-fluoro-2-(3-(1-methyl-1H-pyrazol-4-yl)acrylamido)phenyl)carbamate (0.10 g, 0.28 mmol) in dioxane (2.5 mL). The mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with diethyl ether (20 mL) and the hydrochloride salt of (E)-N-(2-amino-5-fluorophenyl)-3-(1-methyl-1H-pyrazol-4-yl)acrylamide precipitated was filtered. It was suspended in a saturated sodium bicarbonate solution and the mixture was stirred. The solid was filtered and washed with water then dried under vacuum to give the pure product (58 mg) as an off-white solid. ES+(M+H)+261.

Workup

  1. customgroup removal
  2. customthe hydrochloride salt of (E)-N-(2-amino-5-fluorophenyl)-3-(1-methyl-1H-pyrazol-4-yl)acrylamide precipitated
  3. filtrationwas filtered
  4. stirringthe mixture was stirred
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customthen dried under vacuum

Sources & evidence

ORD record
ord-ce053755889d4a32adf42ee302a80972
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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