Hydrochloric Acid → HCID 60198421, compound

HRID 1850051Notes

Reaction equation

HRID 1850051 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([F:35])[CH:34]=1)[O:5][CH2:6][CH2:7][N:8]1[CH:12]=[C:11](/[CH:13]=[CH:14]/[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:24]C(=O)OC(C)(C)C)=[O:16])[CH:10]=[N:9]1.Cl>O1CCOCC1.C(OC(=O)C)C>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:15](=[O:16])/[CH:14]=[CH:13]/[C:11]1[CH:10]=[N:9][N:8]([CH2:7][CH2:6][O:5][C:4]2[CH:32]=[C:33]([F:35])[CH:34]=[C:2]([F:1])[CH:3]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86702814HCID 86702814, compound

Product 1

HCID 60198421HCID 60198421, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (E)-tert-butyl (2-(3-(1-(2-(3,5-difluorophenoxy)ethyl)-1H-pyrazol-4-yl)acrylamido)phenyl)carbamate (113 mg, 0.23 mmol) in dioxane (3 mL) was mixed with a 4 M solution of HCl in dioxane (2 mL). The mixture was stirred for 6 h at room temperature under a nitrogen atmosphere. The reaction mixture was then diluted with ethylaceate (15 mL). The salt was filtered, washed with EtOAc and dried overnight to 92 mg of the hydrochloric acid salt of (E)-N-(2-aminophenyl)-3-(1-(2-(3,5-difluorophenoxy)ethyl)-1H-pyrazol-4-yl)acrylamide as an off-white solid. MS: 1H NMR (CD3OD) δ: 8.07 (s, 1H), 7.86 (s, 1H), 7.70 (d, J=15.4 Hz, 1H), 7.28-7.54 (m, 4H), 6.62 (d, J=15.7 Hz, 1H), 6.45-6.57 (m, 3H), 4.55 (t, J=5.2 Hz, 2H), 4.37 (t, J=5.2 Hz, 2H) ES+(M+Na)+: 407

Workup

  1. filtrationThe salt was filtered
  2. washwashed with EtOAc
  3. dry with materialdried overnight to 92 mg of the hydrochloric acid salt of (E)-N-(2-aminophenyl)-3-(1-(2-(3,5-difluorophenoxy)ethyl)-1H-pyrazol-4-yl)acrylamide as an off-white solid

Sources & evidence

ORD record
ord-5ca904d3965c4aaea7f020f4162588c0
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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