Hydrochloric Acid → HCID 60198482, compound

HRID 1850054Notes

Reaction equation

HRID 1850054 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:16][C:17](=[O:26])/[CH:18]=[CH:19]/[C:20]2[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=2)=[C:6]([NH:8]C(=O)OC(C)(C)C)[CH:7]=1.Cl>O1CCOCC1>[NH2:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[NH:16][C:17](=[O:26])/[CH:18]=[CH:19]/[C:20]1[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86702815HCID 86702815, compound

Product 1

HCID 60198482HCID 60198482, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(E)-tert-butyl (5-fluoro-2-(3-(1-methyl-1H-pyrazol-4-yl)acrylamido)phenyl)carbamate (0.15 g, 0.42 mmol) was dissolved in dioxane (4 mL). A 4M solution of HCl in dioxane (4 mL) was added and the mixture was stirred at room temperature for 3 h. Salt precipitation was observed. The reaction mixture was then diluted with diethyl ether (20 mL) and the crude hydrochloride salt was filtered. It was stirred with saturated sodium bicarbonate (excess) and filtered. The precipitate was washed with water and vacuum dried. (E)-N-(2-amino-4-fluorophenyl)-3-(1-methyl-1H-pyrazol-4-yl)acrylamide (73 mg) was obtained as an off-white solid. 1H NMR (CD3OD) δ: 7.88 (s, 1H), 7.77 (s, 1H), 7.53 (d, J=15.7 Hz, 1H), 7.12 (dd, J=8.5, 5.9 Hz, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.55 (dd, J=10.5, 3.0 Hz, 1H), 6.39 (td, J=8.5, 2.7 Hz, 1H), 3.90 (s, 4H); ES+(M+H)+261.

Workup

  1. customSalt precipitation
  2. additionThe reaction mixture was then diluted with diethyl ether (20 mL)
  3. filtrationthe crude hydrochloride salt was filtered
  4. stirringIt was stirred with saturated sodium bicarbonate (excess)
  5. filtrationfiltered
  6. washThe precipitate was washed with water and vacuum
  7. customdried

Sources & evidence

ORD record
ord-9ca8931a6cfa4747b17ce4692f406fd4
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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